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9780470862988

Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis

by
  • ISBN13:

    9780470862988

  • ISBN10:

    047086298X

  • Edition: 1st
  • Format: Hardcover
  • Copyright: 2005-05-20
  • Publisher: WILEY

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Summary

Since its discovery in 1963 by R. B. Merrifield, solid-phase synthesis, or polymer-supported synthesis, has become an essential technique with its wide use in the synthesis of peptides and other oligomers. Solid-Phase Reactions provides extensive and comprehensive information on this form of synthesis in a format ideal for those working in the laboratory.As part of the Handbook of Reagents in Organic Synthesis Series, this new addition extends the wealth of information available to the chemist at the bench. All content has been expertly collected and presented by an internationally recognised and respected editorial board led by Professor Peter Wipf.

Author Biography

Jonathan A. Ellman is Eugene Higgins Professor of Chemistry at Yale University. He received his B.S. in Chemistry from MIT and his PhD in Organic Chemistry from Harvard University. His research efforts are focused on the development of efficient, systematic chemical tools to establish protein function through the design and synthesis of small molecule libraries targeting protein families, methods for the asymmetric synthesis of amines, and the development of synthetic applications of C-H activation.

Table of Contents

Preface ix
Introduction xi
Recent Review Articles and Monographs 1(6)
4-Acetoxymethylbenzoic Acid
7(1)
N-[(Allyloxycarbonyl)oxy]maleimide-styrene Copolymer (Alloc-resin)
8(1)
Alumina
9(4)
5-[(4-Aminomethyl)-3,5-dimethoxyphenoxy]pentanoic Acid (PAL-linker)
13(1)
3-Amino-3-(2-nitrophenyl)propionic Acid (ANP-linker)
14(2)
O-(7-Azabenzotriazol-1-yl)-1,3-dimethyl-1,3-dimethyleneuronium Hexafluorophosphate (HAMDU)
16(1)
7-Azabenzotriazol-1-yloxytris(dimethylamino) phosphonium Hexafluorophosphate (AOP)
17(2)
(7-Azabenzotriazol-1-yloxy)tris(pyrrolidino) phosphonium Hexafluorophosphate (PyAOP)
19(2)
Azidation Polymer
21(1)
Azidotris(dimethylamino)phosphonium Hexafluorophosphate
22(3)
BEMP Resin (PS-2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine)
25(1)
1,2-Benziodoxol-3(1H)-one, 1-hydroxy, 1-oxide (IBX)
26(4)
1-Benzotriazolyl Diethyl Phosphate (BDP)
30(1)
(1H-Benzotriazol-1-yloxy)tripyrrolidino-phosphonium Hexafluorophosphate (PyBOP)
31(4)
Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate (BOP)
35(4)
O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Hexafluorophosphate (HBTU)
39(1)
O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Tetrafluoroborate (TBTU)
40(3)
Bis(2,4-dinitrophenyl) Carbonate
43(1)
Bis(o-nitrophenyl) Phenylphosphonate
44(1)
Bis(p-nitrophenyl) Phenylphosphonate
45(1)
Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride (BOP-Cl)
45(2)
Bis(pentafluorophenyl)carbonate
47(2)
1,1,3,3-Bis(tetramethylene)chlorouronium Hexafluorophosphate (PyClU)
49(1)
Bis(tricyclohexylphosphine)(4-polystyrylmethylidene)ruthenium Dichloride
50(1)
Borohydride Exchange Resin
51(5)
4-Bromomethyl-3-nitrobenzoic Acid
56(2)
4-(2-Bromopropionyl)phenoxyacetic Acid
58(2)
Bromotripyrrolidinophosphonium Hexafluorophosphate (PyBroP)
60(3)
1,1'-Carbonylbis(3-methylimidazolium) Bis(trifluoromethanesulfonate)
63(1)
N,N'-Carbonyldiimidazole (CDI)
63(4)
Celite
67(1)
6-Chloro-1-(p-chlorobenzenesulfonyloxy)benzotriazole
68(1)
2-Chloro-1,3-dimethylimidazolidium Hexafluorophosphate (CIP)
69(3)
6-Chloro-2,4-dimethoxy-s-triazine (CDMT)
72(2)
Chlorotripyrrolidinophosphonium Hexafluorophosphate (PyClOP)
74(2)
Copper(II) Nitrate - K10 Bentonite Clay
76(1)
Cyanuric Fluoride
77(2)
1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide
79(1)
1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide Metho-p-toluenesulfonate
80(3)
1,3-Dicyclohexylcarbodiimide (DCC)
83(3)
N,N-Diethanolaminomethyl Polystyrene (PS-DEAM)
86(2)
Diethyl Phosphorocyanidate (DEPC)
88(2)
3-(Diethoxyphosphoryloxy)-1,2,3-benzo-trazin-4(3H)-one (DEPBT)
90(3)
1,3-Diisopropylcarbodiimide (DIC)
93(4)
2,4-Dimethoxy-4'-hydroxybenzophenone
97(1)
4-[(2,4-Dimethoxyphenyl){[1-(9H-fluoren-9-ylmethoxy) carbonyl]amino}methyl]phenoxyacetic acid (Rink Amide-linker)
98(4)
N-[(Dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium Hexafluorophosphate N-Oxide (HATU)
102(2)
Diphenyl Phosphorochloridate
104(3)
2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ)
107(1)
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (EDCl)
108(2)
N-Ethyl-5-phenylisoxazolium-3'-sulfonate (Woodward's Reagent K)
110(5)
4-{4-[1-[(9H-Fluoren-9-ylmethoxycarbonyl)amino]ethyl]-2-methoxy-5-nitrophenoxy}butanoic Acid
115(2)
5-[4-(9-Fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy]pentanoic acid (FMOC-PAL-linker)
117(4)
Fluorous Alkoxyethyl Ether (AE(F), [4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)undecyloxy]ethene)
121(2)
Fluorous DEAD
123(2)
Fluorous DMSO (1,1,1,2,2,3,3,4,4-nonafluoro-6-(methanesulfinyl)hexane)
125(1)
Fluorous Tetrahydropyranyl Ether (THP(F), 2-benzenesulfinyl-3-heptadecafluorooctyltetrahydropyran)
126(2)
Fluorous TIPS Triflate
128(1)
4-(4-Formyl-3-methoxyphenoxy)-butanoic Acid (FMPB-linker)
129(2)
4-Hydroxymethylbenzoic acid (HMBA-linker)
131(2)
4-(4-Hydroxymethyl-3-methoxyphenoxy)butyric Acid (HMPB-linker)
133(2)
4-(Hydroxymethyl)phenoxyacetic Acid
135(4)
N-(3-Hydroxy-9H-xanthenyl-O-(9H-fluoren-9-yl)methylcarbamic Acid
139(4)
Iron(III) Chloride-Silica Gel
143(2)
JandaJel
145(6)
Merrifield Resin (Chloromethylcopoly(styrene-divinylbenzene))
151(6)
1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT)
157(4)
N-Methylmorpholine Polystyrene (PS-NMM)
161(2)
Montmorillonite K10
163(4)
Nafion-H
167(2)
2-(5-Norbornene-2,3-dicarboximido)-1,1,3,3-tetramethyluronium Tetrafluoroborate (TNTU)
169(2)
S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium Hexafluorophosphate (HOTT)
171(2)
Ozone-Silica Gel
173(4)
Palladium on Carbon
177(4)
Palladium(II) Hydroxide on Carbon
181(2)
PAMAM Dendrimer Resin (DendroGel)
183(2)
Pd Nanoparticles
185(1)
Pentafluorophenyl Diphenylphosphinate (FDPP)
186(5)
1H,1H,2H,2H-Perfluorodecanethiol (Fluorous Thiol)
191(2)
Phenylbis[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) phenyl]-phosphine (Fluorous Triphenylphosphine)
193(2)
Platinum on Alumina
195(1)
Platinum(IV) Oxide
196(3)
(Polyallyl)scandium Triflylamide Ditriflate (PA-Sc-TAD)
199(1)
3,3'-PolyBINOL
200(2)
Poly[4-(diacetoxyiodo)styrene] (PS-DIB)
202(4)
Poly(ethylene glycol)-supported Burgess Reagent (PEG-Burgess Reagent)
206(2)
Poly(ethylene glycol)-supported 1,4-Phthalazinediyl Diether Hydroquinidine (DHQD)2PHAL Ligand)
208(1)
Poly(ethylene glycol)-supported Dialkylborane
209(1)
Poly(ethylene glycol)-supported N-Phenyl Triflimide
210(1)
Poly(ethylene glycol)-supported Triarylphosphine
211(2)
Poly(exo-N-hydroxy-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboximide) (ROMPGEL-N-Hydroxysuccinimide)
213(2)
Polyhexamethylenecarbodiimide
215(1)
Polymer-bound Diisopropyl Chlorosilane
216(1)
Polymer-bound Dipheny1 Chlorosilane
217(1)
Polymer-bound N-Hydroxysuccinimide
218(3)
Polymer-supported O-Allylisourea
221(2)
Polymer-supported Ammonium Periodate
223(1)
Polymer-supported O-Benzylisourea
224(2)
Polymer-supported Bis(acyloxy)bromate (I)
226(2)
Polymer-supported Bis(acyloxy)iodate (I)
228(3)
Polymer-supported Bis(azido)iodate (I)
231(2)
Polymer-supported Carbonate
233(2)
Polymer-supported Hydroxide
235(2)
Polymer-supported O-Methylisourea
237(2)
Polymer-supported Perruthenate
239(1)
Polymer-supported Sulfonic Acid (Dowex 50W)
240(7)
Polymer-supported Sulfonic Acid (Dowex 50x8)
247(2)
Polymer-supported Tetrathiafulvalene
249(1)
Polymer-supported Thiophenol
250(2)
Polymer-supported p-Toluenesulfonyl Chloride and Related Reagents
252(3)
Polymer-supported 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (PTBD)
255(5)
Polymer-supported Trialkylsilyl Cyanide
260(2)
Polymer-supported Trisamine
262(3)
Polystyrene
265(4)
Polystyrene-bound 1-Hydroxybenzotriazole (PS-HOBT)
269(3)
Polystyrene-bound Dimethylaminopyridine (PS-DMAP)
272(2)
Polystyrene-1-ethyl-3-(3'-dimethylaminopropyl)-carbodiimide Hydrochloride (PS-EDCl)
274(4)
Polystyrene-supported Methylenetriphenylphosphorane
278(3)
Polystyrene-supported Tosyl Azide
281(2)
Polystyrene-supported Triphenylphosphine
283(3)
Polystyrylboronic Acid
286(2)
Poly(4-vinylpyridine)
288(1)
Poly(4-vinylpyridinium Bromide Dichromate
289(1)
Poly(4-vinylpyridinium Bromide Perbromide)
289(1)
Potassium Fluoride--Alumina
290(2)
Potassium Fluoride--Celite
292(1)
Potassium Hydroxide--Alumina
293(1)
Potassium on Alumina
294(1)
N-[(Propargyloxycarbonyl)oxy]maleimidestyrene Copolymer (Proc-resin)
295(1)
Pyridinium Chlorochromate-Alumina
296(2)
2-Pyridyldimethylsilane
298(5)
Rhodium on Alumina
303(4)
Silver(I)carbonate on Celite
307(5)
Solid-supported Phosphine-free Ruthenium Alkylidene for Olefin Metathesis
312(3)
O-(N-Succinimidyl)-1,1,3,3-tetramethyluronium Tetrafluoroborate (TSTU)
315(2)
TEMPO-methyl-polystyrene Resin
317(1)
Tentagel
318(3)
1,1,3,3-Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH)
321(2)
Tetramethylurea
323(2)
Triazene Resin
325(4)
Triphenylmethyl Chloride Resins
329(3)
Triphenylphosphine Selenide
332(1)
Tris(2-perfluorohexylethyl)tin Hydride (Fluorous Tin Hydride)
333(4)
Wang Resin
337(4)
List of Contributors 341(10)
Reagent Formula Index 351(4)
Subject Index 355

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