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Handbook of Reagents for Organic Synthesis, Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis

ISBN: 978-0-470-86298-8
392 pages
May 2005
Handbook of Reagents for Organic Synthesis, Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis (047086298X) cover image
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.

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Preface.

Introduction.

Recent Review Articles and Monographs.

4-Acetoxymethylbenzoic Acid.

N-[(Allyloxycarbonyl)oxy]maleimide-styrenne Copolymer (Alloc-resin).

Alumina.

5-[(4-Aminomethyl)-3,5-Dimethoxyphenoxy] Pentanoic Acod (PAL-Linker).

3-Amino-3-(2-nitrophenyl)propionoc Acid (ANP-linker).

0-(7-Azabenzotriazol-1-yl)-1,3-dimethyl-1,3-dimethylleneuronium hexafluorophosphate (HAMDU).

7-Azabenzotriazol-1-yloxytris(dimethyamino) phosphonium hexafluorosphate (AOP).

(7-Azabenzotriazol-1-yloxy)tris(pyrrolidino) phosphonium Hexafluorophosphate (pyAOP).

Azidation Polymer.

Azidotris(dimethylamino)phosphonium.

Hezafluorophosphate.

BEMP resin (PS-2-tert-butylimino-2-dimethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine).

1,2-Benziodoxol-3(1H)-one,1-hydroxy,1-oxide (IBX).

1-Benzotriazolyl Diethyl Phosphate (BDP).

 (1H-Benzotriazol-1-yloxy)tripyrrolodino-phosphonium Hexafluorophosphate (pyBOP).

Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate (BOP).

O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Hexafluorophosphate (HBTU).

O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Tetrafluoroborate.

Bis(2,4-dinitrophenyl) Carbonate.

Bis(o-nitrophenyl) Phenylphosphonate.

Bis(p-nitrophenyl) Ohenylphosphonate.

Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride (BOP-CI).

Bis(pentafluorophenyl)carbonate.

1,1,3,3-Bis(tetramethylene)chlorouronium Hexafluorophosphate (pyCIU).

Bis(tricyclohexyphosphine)(4-polystyrylmethylidene) ruthenium Dichloride.

Borohydride Exchange Resin.

4-Bromomethyl-3-nitrobenzoic Acid.

4-(2-Bromopropionyl)phenoxyacetic Acid.

Bromotripyrrolodinophosphonium Hexafluorophosphate (pyBroP).

1,1'-Carbonylbis(3-methylimidazolium) Bis(trifluoromethanesulfonate).

N,N'-carbonydiimidazole (CDI).

Celite.

6-Chloro-1-(p-chlorobenzenesulfonyloxy) benzotriazole.

2-Chloro-1,3-demthylimidazolidium Hezafluorophosphate (CIP).

6-Chloro-2,4-dimethyoxy-s-triazine (CDMT).

Chlorotripyrrolidinophosphonium Hexafluorophosphate (pyCIOP).

copper(II) Nitrate - K10 Bentonite Clay.

Cyanuric Flouride.

1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide.

1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide methop-toluenesulfontae.

1,3-Dicyclohexylcarbodiimide (DCC).

N,N-Diethanolaminomethyl Polystyrene (PS-DEAM).

Diethyl phosphorocyanidate (DEPC).

3-(Diethoxyphosphoryloxy)-1,2,3-benzo-trazin-4(3H)-one (DEPBT).

1,3-Diisopropylcarbodiimide (DIC).

2,4-Dimethoxy-4'-hydroxybenzophenone.

4-[(2,4-Dimethoxyphenyl){[1-(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl]phenoxyacetric Acid (Rink Amide-linker).

N-[(Dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium.

Hexafluorophosphate N-Oxide (HATU).

Diphenyl phosphorochloridate.

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ).

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (EDCI).

N-Ethyl-5-phenylisoxazolium-3'-sulfonate (Woodward's Reagent K).

4-{4-[1-[(9H-Fluoren-9-ylmethoxycarbonyl)amino]ethyl]-2-methoxy-5-nitrophenoxy}butanoic Acid.

5-[4-(9-Fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy]pentanoic acid (FMOC-PAL-linker).

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-heptadecfluoro-                                 decyl)undecyloxy]ethene).         

Fluorous DEAD.

Fluorous DMSO (1,1,1,2,2,3,3,4,4-nonafluoro-6-(methanesulfinyl)hexane).

Fluorous Tetrahydropyranyl Ether (THP(F),                                                    2-benzenesulfinyl-3-heptadecafluorooctyltetrahydropyran). 

Fluorous TIPS Triflate.

4-(4-Formyl-3-methoxyphenoxy)-butanoic Acid                                       (FMPB-linker).       

4-Hydroxymethylbenzoic acid (HMBA-linker).

4-(4-Hydroxymethyl-3-methoxyphenoxy)butyric Acid (HMPB-linker).

4-(hydroxymethyl)phenoxyacetic Acid.

N-(3-Hydroxy-9Hxanthenyl-O-(9H-fluoren-9-yl)methylcarbamic Acid.

Iron(III) Chloride-Silica Gel.

JandaJel.

Merrifield Resin (chloromethylcopoly(styrene-divinylbenzene)).

1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT).

N-Methylmorpholine Polystyrene (PS-NMM).

Montmorillonite K10.

Nafion-H.

2-(5-Norbornene-2,3-Dicarboximido_1,1,3,3-tetramethyluronium Tetrafluoroborate (TNTU).

S-(1-Oxido-2-pirydinyl)-1,13,3-tetramethylthiouronium Hexafluorophosphate (HOTT).

Ozone-Silica Gel.

Palladium on Carbon.

Palladium(II) Hydroxide on Carbon.

PAMAM Dendrimer Resin (DendroGel).

pd Nanoparticles.

Pentafluorophenyl Diphenylphosphinate (FDPP).

1H,1H,2H,2H-perfluorodecanethiol (Fluorous Thiol).

phenylbis[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) phenyl]-phosphine (Fluorous Triphenylphosphine.

Platinum on Alumina.

Platinium (IV) Oxide.

(polyallyl)scandium Triflylamide Ditriflate (PA-Sc-TAD).

3,3'-polyBINOL.

poly[4-(diacetoxyiodo)styrene](PS-DIB).

poly(ethylene glycol)-supported burgess reagent (PEG-Burgess Reagent).

poly(ethylene glycol)-supported 1,4-phthalazinediyl Diether Hydroquinidine ((DHQD)2 PHAL Ligand).

poly(ethylene glycol)-supported Dialkylborane.

poly(ethylene glycol)-supported N-phenyl Triflimide.

poly(ethylene glycol)-supported Thiarylphosphine.

poly(exo-N-Hydroxy-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboximide) (ROMPGEL-N-Hydroxysuccinimide).

Polyhexamethylenecarbodiimide.

Polymer-bound Diisopropyl Chlorosilane.

Polymer-bound Diphenyl Chlorosilane.

Polymer-bound N-Hydroxysuccinimide.

Polymer-supported O-Allyisourea.

Polymer-supported Ammonium Periodate.

Polymer-supported O-Benzylisourea.

Polymer-supported Bis(acyloxy)bromate(I).

Polymer-supported Bis(acyloxy)iodate (I).

Polymer-supported Bis(azido)iodate(I).

Polymer-supported Carbonate.

Polymer-supported Hydroxide.

Polymer-supported O-Methylisourea.

Polymer-supported Perruthenate.

Polymer-supported Sulfonic Acid (Dowex 50W).

Polymer-supported Sulfonic Acid (Dowex 50x8).

Polymer-supported Tetrathiafulvalene.

Polymer-supported Thiophenol.

Polymer-supported p-Toluenesulfonyl Chloride and related reagents.

Polymer-supported 1,5,7-Triazabicyclo[4.4.0]dec-5-ene PTBD).

Polymer-supported Trialkylsilyl Cyanide.

Polymer-supported Trisamine.

Polystyrene.

Polystyrene-bound 1-Hydroxybenzotriazole (PS-HOBT).

Polystyrene-bound Dimethylaminopyradine (PS-DMAP) carbodiimide Hydrochloride (PS-EDCI).

Polystyrene-supported Methyleneriphenylphosphorane.

Polystyrene-supported Tosyl Azide.

Polystyrene-supported Triphonylphosphine.

Polystyrylboronic Acid.

Poly(4-vinylpyridine).

Poly(4-vinylpyridinium Bromide Dichromate).

Poly(4-vinylpyridinium Bromide Perbromide).

Potassium Flouride-Alumina.

Potassium Flouride-Celite.

Potassium Hydroxide-Alumina.

Potassium on Alumina.

N-[(Propargyloxycarbonyl)oxy]maleimidestyrene Copolymer (Proc-resin).

Pyridinium Chlorochromate-Alumina.

2-Pyridyldimethylsilane.

Rodium on Alumina.

Silver(I) Carbon on Celite.

Solid-supported Phosphine-free Ruthenium Alkylidene for Olefin Metathesis.

O-(N-Succinimidyl)-1,1,3,3-Tetramethyluronium Tetrafluoroborate (TSTU).

TEMPO-methyl-polystyrene resin Tentagel.

1,1,3,3-Tetramethylfluoroformamidinum Hexafluorophosphate (TFFH).

Tetramethylurea.

Triazene resin.

Triphenylmethyl Chloride resins.

Triphenylphosphine Selenide.

Tris(2-perfluorohexylethyl)tin Hydride (Fluorous Tin Hydride).

Wang Resin.

List of Contributers.

Reagent Fomula Index.

Subject Index.

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"…a very useful compendium...this volume will interest any institution where synthetic organic chemical and biochemical research is carried out." (CHOICE, January 2006)

"...a valuable resource and of high interest..." (Journal of Medicinal Chemistry, Vol 48 (20) 2005)

"...this volume will be an invaluable reference source..." (Applied Organometallic Chemistry, Vol 19 (12), December 2005)

"…an excellent starting point…or as a solid ready-reference source for the more experienced user." (Journal of Natural Products, November 2005)

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Encyclopedia of Reagents  for Organic Synthesis

The ultimate online information on reagents, critically selected, edited and updated by leading organic chemists. Includes data on 3600 reagents and 49000 reactions.

Visit e-EROS at www.interscience.wiley.com/eros 

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