Reagents for glycoside, nucleotide, and peptide synthesis / ed. by D.Crich. - Hoboken: Wiley, 2005. - ix, 770 p. - (Handbook of reagents for organic synthesis). - Ind.: p.721-770. - ISBN 978-0470-02304-4  Место хранения:   032 | Институт органической химии им. Н.Н.Ворожцова СО РАН | Новосибирск | Библиотека

Оглавление / Contents

Preface ........................................................ ix Introduction ................................................... xi Recent Review Articles and Monographs ........................... 1 Acetonitrile .................................................... 9 p-Acetoxybenzyl Bromide ........................................ 15 2-[(l-Acetyl-2-oxopropyl)thio]-lff-isoindole-l,3(2H)-dione ..... 16 2-Adamantyl Chloroformate ...................................... 19 N-[(Allyloxycarbonyl)oxy]maleimide-styrene Copolymer (Alloc-resin) .................................................. 20 Allyl Tetraisopropylphosphoramidite' ........................... 21 Allyl Trichloroacetimidate ..................................... 27 Anthracenesulfonamide .......................................... 29 O-(7-Azabenzotriazol-1-yl)-1,3-dimethyl-1,3- dimethyleneuronium Hexafluorophosphate ......................... 31 (7-Azabenzotriazol-1-yloxy)tris(pyrrolidino)phosphonium Hexafluorophosphate ............................................ 33 7-Azabenzotriazol-1-yloxy tris(dimethylamino)phosphonium Hexafluorophosphate ............................................ 35 Azidotris(dimethylamino)phosphonium Hexafluorophosphate ........ 36 Benzeneselenenyl Bromide ....................................... 39 Benzeneselenenyl Trifluoromethanesulfonate ..................... 53 Benzenesulfenyl Chloride ....................................... 60 Benzenesulfenyl Trifluoromethanesulfonate ...................... 70 1-Benzenesulfinyl Piperidine ................................... 72 Benzimidazolium Trifluoromethanesulfonate ...................... 74 3H-1,2-Benzodithiol-3-one 1,1 -Dioxide ......................... 77 1,3-Benzodithiol-1-ium Tetrafluoroborate ....................... 80 Benzothianthrene Oxide ......................................... 81 3H-1,2-Benzothiaselenol-3-one .................................. 83 Benzothiazole-2-sulfonyl Chloride (BtsCl) ...................... 84 1-Benzotriazolyl Diethyl Phosphate (BDP) ....................... 85 Benzotriazol-1-yloxy tris(dimethylamino)phosphonium Hexafluorophosphate (BOP) ...................................... 86 (1H-Benzotriazol-l-yloxy)tris(pyrrolidino)phosphonium Hexafluorophosphate ............................................ 88 O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Hexafluorophosphate ............................................ 92 O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Tetrafluoroborate .............................................. 94 Benzyl Bromide ................................................. 96 Benzyl Chloroformate ........................................... 98 Benzyl 2-Hydroxymethylbenzoate ................................ 101 Benzyl Isopropenyl Ether ...................................... 103 Benzyl 2,2,2-Trichloroacetimidate ............................. 103 N,N'-Bis(t-butoxycarbonyl)-N''-Trifluoromethanesulfonyl Guanidine ..................................................... 105 1,3-Bis(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbodiimide (BDDC) ........................................................ 107 Bis(2,4-dinitrophenyl) Carbonate .............................. 108 Bis(1-methoxy-2-methyl-1-propenyloxy)dimethylsilane ........... 109 N-Bis(methylthio)memylene-p-toluenesulfonamide ................ 110 Bis(4-nitrophenyl) Carbamate .................................. 119 Bis(p-nitrophenyl) Hydrogen Phosphate ......................... 120 Bis(o-nitrophenyl) Phenylphosphonate .......................... 121 Bis(p-nitrophenyl) Phenylphosphonate .......................... 121 Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride .................. 122 Bis(pentafluorophenyl) Carbonate .............................. 124 Bis(o-phenylene) Pyrophosphate ................................ 125 1,2-Bis(phenylsulfonyl)ethylene ............................... 126 1,1,3,3-Bis(tetramethylene)chlorouronium Hexafluorophosphate ........................................... 131 Bis(tributyltin) Oxide ........................................ 132 Bis(2,2,2-trichloroethyl) Azodicarboxylate .................... 134 Bis(2,2,2-trichloroethyl) Phosphorochloridate ................. 135 Bis(trichloromethyl) Carbonate ................................ 137 2,7-Bis(trimethylsilyl)fluorenylmethyl Chloroformate .......... 138 p-Bromobenzyl Bromide ......................................... 139 3-Bromocyclohexene ............................................ 141 2-Bromo-1-ethylpyridinium Tetrafluoroborate (ВЕР) ............. 142 Bromonium Di-sym-collidine Perchlorate ....................... 143 N-Bromosuccinimide ............................................ 145 Bromotripyrrolidinophosphonium Hexafluorophosphate ............ 150 1-N-(t-Butoxycarbonyl)-1H-benzotriazole-3N-oxide .............. 153 1-(t-Butoxycarbonyl)imidazole ................................. 154 2-(t-Butoxycarbonyloxyimino)-2-phenylacetonitrile ............. 154 t-Butyl Chloroformate ......................................... 156 Cadmium Carbonate ............................................. 159 Carbomethoxysulfenyl Chloride ................................. 159 1,1'-Carbonylbis(3-methylimidazolium) Bis(trifluoromethanesulfonate) ................................ 165 N,N'-carbonyldiimidazole ...................................... 166 Chloroacetyl Chloride ......................................... 169 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one .................. 176 p-Chlorobenzyl Bromide ........................................ 179 6-Chloro-2,4-dimethoxy-s-triazine ............................. 180 2-Chloro-1,3-dimethylimidazolidium Hexafluorophosphate ........ 182 2-Chloro-1-methylpyridinium Iodide ............................ 185 2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane ........... 187 1-Chloro-N,N,2-trimethylpropenylamine ......................... 188 Chlorotripyrrolidinophosphonium Hexafluorophosphate ........... 191 2,4,6-Collidine ............................................... 192 2-Cyanoethyl Diisopropylchlorophosphoramidite ................. 194 2-Cyanoethylphosphoric Acid ................................... 199 2-Cyanoethyl Tetraisopropylphosphorodiamidite ................. 201 Cyanuric Fluoride ............................................. 227 Cyclohexyl Chloroformate ...................................... 229 l-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide ................ 231 1-Сус1оЬеху1-3-(2-morpholinoethyl)carbodiimide Metho-p- toluenesulfonate .............................................. 232 17H-Cyclopental[1,2-1,:2,4-1']diphenanthren-17-yl Chloroformate ................................................. 233 α-Cyclopropylcyclopropanemethanol ............................. 234 Dibenzyl N,N-Diisopropylphosphoramidite ....................... 235 Dibenzylphosphite ............................................. 238 2,7-Dibromo-9H-fluoren-9-ylmethyl Chloroformate ............... 239 Dibromomethylbenzene .......................................... 242 Dibromomethyl Methyl Ether .................................... 244 Di-t-butyl Dicarbonate ........................................ 247 2,7-Di-t-Butyl-9-fluorenylmethyl Chloroformate ................ 254 2,6-Di-t-butylmethylpyridine .................................. 255 Di-n-butyltin Oxide ........................................... 260 Dichlorobis(cyclopentadienyl)hafnium-Silver(I) Salts .......... 265 Dichloromethyl Methyl Ether ................................... 267 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane ................. 270 4,5-Dicyanoimidazole .......................................... 271 1,3-Dicyclohexylcarbodiimide .................................. 274 1.3-Dicyclohexylcarbodiimide-4-dimethylaminopyridine .......... 277 3-(Diethoxyphosphoryloxy)-1,2,3-benzotrazin-4(3H)-one (DEPBT) ....................................................... 278 Diethyl Chlorophosphite ....................................... 280 Diethyl Phosphorochloridate ................................... 288 Diethyl Phosphorocyanidate (DEPC) ............................. 291 3.4-Dihydro-2H-pyrido[1,2-α]pyrimidin-2-one ................... 293 1,3-Diisopropylcarbodiimide ................................... 294 2-(Dimethoxymethyl)naphthalene ................................ 298 2,2-Dimethoxypropane .......................................... 300 4,4'-Dimethoxytrityl Chloride ................................. 301 N-[(Dimethylamino)-1H-l,2,3-triazolo[4,5-b]pyridin-1- ylmethylene]-N-methylmethanaminium Hexafluorophosphate N-Oxide ....................................................... 304 α,α-Dimethyl Cyclopropanemethanamine .......................... 306 Dimethyl(methylthio)sulfonium Tetrafluoroborate ............... 307 Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate ....... 313 Dimethylphosphinothioyl Chloride .............................. 317 Diphenylphosphinic Chloride ................................... 318 Diphenyl Phosphonate .......................................... 319 Diphenyl Phosphorazidate ...................................... 322 Diphenyl sulfoxide ............................................ 324 Di-2-pyridyl Carbonate ........................................ 329 2,2'-Dipyridyl Disulfide ...................................... 330 2,2'-Dipyridyl Disulfide-N,N'-Dioxide ......................... 338 N-Ethoxycarbonyl Phthalimide .................................. 343 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline ................ 344 N-Ethylbenzisoxazolium Tetrafluoroborate ...................... 345 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride ................................................. 347 N-Ethyl-5-phenylisoxazolium-3'-sulfonate (Woodward's Reagent K) .................................................... 349 5-Ethylthio-1H-tetrazole ...................................... 351 9-Fluorenylmethyl Chloroformate ............................... 355 N-(9-Fluorenylmethyloxycarbonyl)oxybenzotriazole (Fmoc-HOBT) ................................................... 357 N-(9-Fluorenylmethyloxycarbonyl)oxysuccinimide ................ 359 O-(9-HuorenyImethyloxycarbonyl) Pentafluorophenol ............. 361 Hexafluorophenylpropanol ...................................... 365 2,5-Hexanedione ............................................... 366 N-Hydroxybenzotriazole ........................................ 370 2-Hydroxyethyl Phenyl Sulfone ................................. 372 N-Hydroxysuccinimide .......................................... 375 1-Hydroxy-l,2,3-triazole-4-carboxylate ........................ 376 Iodine Azide .................................................. 379 Iodine Monobromide ............................................ 384 Iodine Monochloride ........................................... 386 p-Iodobenzyl Bromide .......................................... 390 Iodonium Di-sym-collidine Perchlorate ......................... 391 Iodonium Di-sym-collidine Trifluoromethanesulfonate ........... 395 2-(2-Iodophenyl)ethanethiol ................................... 396 N-Iodosaccharin ............................................... 398 N-Iodosuccinimide ............................................. 399 Isobutyl Chloroformate ........................................ 402 Isopropenyl Chloroformate ..................................... 404 Levulinic Anhydride ........................................... 409 6-Mercapto-4-dibenzofuranol ................................... 413 Mercuric Bromide .............................................. 415 Mercuric Cyanide .............................................. 417 Mesitylenesulfonyl Chloride ................................... 419 1-(Mesitylene-2-sulfonyl)-3-nitro-l,2,4-triazole (MSNT) ....... 421 Mesitylsulfonyl-1H-1,2,4-triazole ............................. 424 p-Methoxybenzyl Chloride ...................................... 425 Methoxyphenyl Benzenethiosulfinate (MPBT) ..................... 428 1-(4-Methoxyphenyl)-2-(4'-methylbenzylthio)ethylamine ......... 429 2-Methoxypropene .............................................. 432 4-Methoxytriphenylmethyl Chloride ............................. 434 TY-Methylcarbazole ............................................ 437 Methyl Trifluoromethanesulfonate .............................. 439 2-Methyl-1-(1-methylethyl)propyl Chloroformate (Doc-Cl) ....... 448 N-Methylmorpholine ............................................ 449 N-Methylmorpholine Polystyrene (PS-NMM) ....................... 453 2-Methylsulfonyl-3-phenyl-l-prop-2-enyl Chloroformate ......... 456 5-Methylthio-1H-tetrazole ..................................... 457 2-Naphthylmethyl Bromide ...................................... 459 p-Nitrobenzenesulfonyl-4-nitroimidazole ....................... 461 o-Nitrobenzyl Bromide ......................................... 461 p-Nitrobenzyl Bromide ......................................... 463 p-Nitrophenol ................................................. 467 5-(4-Nitrophenyl)-1H-tetrazole ................................ 468 Nitrosonium Tetrafluoroborate ................................. 470 2-(5-Norbornene-2,3-dicarboxamido)-1,1,3,3- Tetramethyluronium Tetrafluoroborate .......................... 474 Octenediol .................................................... 477 S-(1-Oxido-2-pyridinyl)-1,1,3,3-Tetramethylthiouronium Hexafluorophosphate (HOTT) .................................... 479 Pentafluorophenol ............................................. 481 Pentafluorophenyl Diphenylphosphinate (ГОРР) .................. 484 4-Pentenoic Acid .............................................. 489 4-Pentenol .................................................... 491 Phenyl-Bis(thiophenyl)sulfonium Hexachloroantimonate .......... 495 Phenyl Chlorothionocarbonate .................................. 496 1,2-Phenylene Phosphorochloridate ............................. 498 Phenyl N-Phenylphosphoramidochloridate ........................ 499 Phenyl Phosphorodi(l-imidazolate) ............................. 502 2-(Phenylseleno)-1H-isoindole-1,3(2H)-dione ................... 503 (2-Phenylsulfonyl)ethoxy Dichlorophosphine .................... 508 2-Phenylthioethanol ........................................... 509 N-Phenyltrifluoroacetimidoyl Chloride ......................... 510 Phosphorus Oxychloride ........................................ 512 Phthalic Anhydride ............................................ 516 Polyhexamethylenecarbodiimide ................................. 520 Polystyrene-bound Dimethylaminopyridine (PS-DMAP) ............. 521 Polystyrene-bound 1-Hydroxybenzotriazole (PS-HOBT) ............ 523 Polymer-bound N-Hydroxysuccinimide ............................ 525 Polystyrene-1-ethyl-3-(3'-dimethylaminopropyl)-carbodiimide Hydrochloride (PS-EDCI) ....................................... 529 Polystyrylboronic Acid ........................................ 533 Potassium Ethyl Xanthate ...................................... 535 N-[(Propargyloxycarbonyl)oxy]maleimide-styrene Copolymer (Proc-resin) .................................................. 544 Pyridine-2-thiol .............................................. 545 H-Pyrophosphonic Acid ......................................... 549 Silver Oxide .................................................. 553 Silver Salicylate ............................................. 556 Silver Silicate ............................................... 559 Silver(I) Tetrafluoroborate ................................... 561 Silver Trifluoromethanesulfonate .............................. 569 O-(N-Succinimidyl)-1,1,3,3-tetramethyluronium Tetrafluoroborate (TSTU) ...................................... 574 9-(2-Sulfo)fluorenylmethyloxycarbonyl Chloride ................ 575 Tetrachlorophthalic Anhydride ................................. 577 Tetrachlorophthalimide ........................................ 580 Tetraethyl Pyrophosphate ...................................... 583 3,3',4,4'-Tetrahydro-6,6'-bi(2H-pyran) ........................ 584 1,1,2,2-Tetramethoxycyclohexane ............................... 586 Tetramethylfluoroformamidinium Hexafluorophosphate ............ 587 Tetramethylurea ............................................... 589 lH-Tetrazole .................................................. 591 1,1'-Thiocarbonyldiimidazole .................................. 593 1,1'-Thionylimidazole ......................................... 595 2-Thiopyridyl Chloroformate ................................... 597 Tin (IV) Chloride ............................................. 598 Tin(II) Chloride-Silver(I) Perchlorate ........................ 613 Tin(II) Trifluoromethanesulfonate ............................. 614 p-Tolyldiphenylmethyl Chloride ................................ 617 1,2,4-Triazole ................................................ 618 Tri-t-butylpyridine ........................................... 619 Tri-t-butylpyrimidine ......................................... 622 Trichloroacetonitrile ......................................... 623 Triethylsilyl Trifluoromethanesulfonate ....................... 628 Trifluoromethanesulfonic Anhydride ............................ 629 m-Trifluoromethylbenzoyl Chloride ............................. 642 Trimethylphosphine ............................................ 644 Trimethylsilyl Trifluoromethanesulfonate ...................... 647 Triphenylcarbenium Tetrafluoroborate .......................... 651 Triphenylchloromethane ........................................ 654 Triphenylmethyl Perchlorate ................................... 660 Triphenylphosphine-N-Bromosuccinimide ......................... 661 Triphenylphosphine Carbon Tetrabromide ........................ 662 Triphenylphosphine Carbon Tetrachloride ....................... 664 Triphenylphosphine Dibromide .................................. 667 Triphenylphosphine Diethylazodicarboxylate .................... 673 Triphenylphosphine Hydrobromide ............................... 683 Triphenylphosphine Selenide ................................... 685 Tris(dimethylamino)phosphine Carbon Tetrabromide .............. 687 Trityl Tetrakis(pentafluorophenyl)borate ...................... 688 Zinc Bromide .................................................. 691 Zinc Chloride ................................................. 695 List of Contributors .......................................... 705 Reagent Formula Index ......................................... 721 Subject Index ................................................. 727