Reagents for Glycoside, Nucleotide, and Peptide Synthesis

ISBN-13: 9780470023044 / Angielski / Twarda / 2005 / 768 str.

David Crich

Opis

This handbook collects together short, informative articles on approximately 250 of the most widely used reagents in the field, into a single volume. Each of the articles, drawn from the e-EROS database, contains a summary of the most pertinent reactions for every reagent, with references to the original literature. This handbook will have a broad appeal and should find a home in every organic chemistry laboratory and library.

• Compiles all the essential reagents for syntheses on and with biomolecules
• Gives key information on protection, bond formation and deprotection
• An essential resource for all synthetic chemists working in drug development and medicinal chemistry
• Makes use of the leading reagent database e-EROS

Recenzje

" recommended for all laboratories working in the areas of organic synthesis, medicinal chemistry or natural product chemistry." ( E–STREAMS, September 2007)

" a very valuable, encyclopedic addition to virtually any organic / synthetic / medicinal chemistry laboratory." (Journal of Medicinal Chemistry, 2006, Vol. 49, No. 7)

"A high caliber reference work" (organic–chemistry.org, August 06)

Spis treści

Preface.

Introduction.

Recent review Artilces and Monogrpahs.

Acetonitrile.

p–Acetoxybenzyl Bromide.

2–[(1–Acetyl–2–oxopropyl)thio]–1H–isoindole–1,3(2H)–dione.

2–Adamantyl Chloroformate.

N–[(Allyloxycarbonyl)oxy]maleimide–styrene Copolymer (Alloc–resin).

Allyl Tetraisopropylphosphoramidite.

Allyl Trichloroacetimidate.

Anthracenesulfonamide.

O–(7–Azabenzotriazol–1–yl)–1,3–dimethyl–1,3–dimethyleneuronium Hexafluorophosphate.

(7–Azabenzotriazol–1–yloxy)tris(pyrrolidino)phosphonium Hexafluorophosphate.

Axidotris(dimethylamino Phosphonium Hexafluorophosphate.

7–Azabenzotriazol–1–yloxytris(dimethylamino)Phosphonium Hexafluorophosphate.

Azidotris(dimethylamino)Phosphonium.

Hexafluorophosphate.

Benzeneselenenyl Bromide.

Benzeneselenenyl Trifluoromethanesulfonate.

Benzenesulfenyl Chloride.

Benzenesulfenyl Trifluoromethanesulfonate.

1–Benzenesulfinyl Piperidine.

Benzimidazolium Trifluoromethanesulfonate.

3H–1,2–Benzodithiol–3–one 1, 1–Dioxide.

1, 3–Benzodithiol–1–ium Tetrafluoroborate.

Benzothianthrene Oxide.

3H–1,2–Benzothiaselenol–3–one.

Benzothiazole–2–sulfonyl chloride (BtsC1).

1–Benzotriazolyl Diethyl Phosphate (BDP).

Benzotriazol–1–yloxytris(dimethylamino)phosphonium.

Hexafluorophosphate (BOP).

(1H–Benzotriazol–1–yloxy)tris(pyrrolidino)phosphonium.

Hexafluorophosphate.

O–Benzotriazol–1–yl–N,N,N′,N′–tetramethyluronium.

Hexafluorophosphate.

O–Benzotriazol–1–yl–N,N,N′,N′–tetramethyluronium.

Tetrafluoroborate.

Benzyl Bromide.

Benzyl Chloroformate.

Benzyl 2–Hydroxymethylbenzoate.

Benzyl Isopropenyl Ether.

Benzyl 2,2,2,–Trichloroacetimidate.

N,N′–Bis(t–butoxycarbony1)–N′–Trifluoromethanesulfonyl Guanidine.

1,3 Bis(2,2–dimethyl–1,3–dioxolan–4–ylmethyl)carbodiimide(BDDC).

Bis(2,4–dinitrophenyl)Carbonate.

Bis(1–methoxy–2–methyl–1–propenyloxy)dimethylsilane.

N–Bis(methylthio)methylene–p–toluenesulfonamide.

Bis(4–nitrophenyl)Carbamate.

Bis(p–nitrophenyl) Hydrogen Phosphate.

Bis(o–nitrophenyl)Phenylphosphonate.

Bis(p–nitrophenyl)Phenylphosphonate.

Bis(2–oxo–3–oxazolidinyl)Phosphinic Chloride.

Bis(pentafluorophenyl)Caronate.

Bis(o–phenylene)Pyrophosphite.

1,2–Bis(phenylsulfonyl)ethylene.

1,1,3,3–Bis9tetramethylene)chlorouronium.

Hexafluorophosphate.

Bis(tributyltin)Oxide.Bis(2,2,2–trichloroethyl)Azodicarboxylate.

Bis(2,2,2–trichloroethyl)Phosphorochloridate.

Bis(trichloromethyl)carbonate.

2,7–Bis(trimethylsily)Fluorenylmethyl Chloroformate.

p–Bromobenzyl Bromide.

3–Bromocyclohexene.

2–Bromo–1–ethylpyridinium Tetrafluoroborate (BEP).

Bromonium Di–sym–collidine Perchlorate.

N–Bromosuccinimide.

Bromotripyrrolidinophosphonium Hexafluorophosphate.

1–N–(t–Butoxycarbonyl)–1H–benzotriazole–3N–oxide.

1–(t–Butoxycarbonyl)imidazole.

2–(t–Butoxycarbonyloxyimino)–2–phenylacetonitrile.

t–Butyl Chloroformate.

Cadmium Carbonate.

Carbomethoxysulfenyl Chloride.

1,1′–Caronylbis(3–methylimidazolium).

Bis(trifluoromethanesulfonate).

N,N′–Carbonyldiimidazole.

Chloroacety Chloride.

2–Chloro–4H–1,3,2–benzodioxaphosphorin–4–one.

p–Chlorobenzyl Bromide.

6–Chloro–2,4–dimethoxy–s–triazine.

2–Chloro–1,3–dimethylimidazolidium Hexafluorophosphate.

2–chloro–1–methylpyridinium Iodide.

2–Chloro–4,4,5,5–ttramethyl–1,3,2–dioxaphospholane.

1–Chloro–N,N,2–trimethylpropenylamine.

ChlorotripyrrolidmopnospnoniumHexafluorophosphate.

2,4,6–Collidine.

2–Cyanoethyl Diisopropylchlorophosphoramidite.

2–cyanoethylphosphoric Acid.

2–Cyanoethyl Tetraisopropylphosphorodiamidite.

Cyanuric Fluoride.

Cyclohexyl Chloroformate.

1–Cyclohexyl–3–(2–morpholineothyl)carbodiimide.

1–Cyclohexyl–3–(2–morpholinoethyl)Carbodiimide.

Metho–p–toluenesulfonate.

17H–Cyclopental[1,2–1,:2,4–1′]diphenanthren–17–yl

Chloroformate.

a–Cyclopropylcyclopropanemethanol.

Dibenzyl N,N–Diisopropylphosphoramidite.

Dibenzylphosphite.

2,7,–Dibromo–9H–Fluoren–9–Ylmethyl Chloroformate.

Dibromomethylbenzene.

Dibromomethyl Methyl Ether.

Di–t–butyl Dicarbonate.

2,7–Di–t–Butyl–9–fluorenylmethyl Chloroformate.

2,6–Di–t–butylmethylpryridine.

Di–n–butyltin Oxide.

Dichlorobis(cyclopentadienyl)hafnium–Silver(I) Salts.

Dichloromethyl Methyl Ether.

1,3–Dichloro–1,1,3,3–tetraisopropyldisiloxane.

4,5–Dicyanoimidazole.

1,3–Dicyclohexylcarbodiimide.

1,3,–Dicyclohexylcarbodiimide–4–dimethylaminopyridine.

3–(Diethoxyphosphoryloxy)–1,2,3–benzotrazin–4(3H)–one (DEPBT).

Diethyl Chlorophosphite.

Diethyl Phosphorochloridate.

Diethyl Phosphorocyanidate (DEPC).

3,4–Dihydro–2H–pyrido[1,2–a]pyrimidin–2–one.

1,3–Diisopropylcarbodiimide.

2–(Dimethoxymethyl)naphthalene.

2,2–Dimethoxypropane.

4,4–Dimethoxytrityl Chloride.

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

Hexafluorophosphate N–Oxide.

a,a–Dimethyl Cyclopropanmethanamine.

Dimethyl(methylthio)sulfonium Tetrafluoroborate.

Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate.

Dimethylphosphinothjoyl Chloride.

Diphenylphosphinic Chloride.

Diphenyl Phosphonate.

Diphenyl Phosphorazidate.

Diphenyl sulfoxide.

Di–2–pyridyl Carbonate.

2,2′–Dipyridyl Disulfide.

2,2′–Dipyridyl Disulfide–N,N′–Dioxide.

N–ethoxycarbonyl Phthalimide.

2–Ethoxy–1–ethoxycarbonyl–1,2–dihydroquinoline.

N–Ethylbenzisoxazolium Tetrafluoroborate.

1–Ethyl–3–(3′–dimethylaminopropyl)Carbodiimide.

hydrochloride.

N–Ethyl–5–phenylisoxazolium–3′sulfonate (Woodward′s Reagent K).

5–Ethylthio–1H–tetrazole.

9–Fluorenylmethyl Chloroformate.

N–(9–Fluorenylmethyloxycarbonyl)oxybenzotriazole(Fmoc–HOBT).

N–(9–Fluorenylmethyloxycaronyl)oxysuccinimide.

O–(9–Fluorenylmethyloxycaronyl)Pentafluorophenol.

Hexafluoreophenylpropanol.

2,5–Hexanedione.

N–Hydroxybenzotriazole.

2–Hydroxyethyl Phenyl Sulfone.

N–Hydroxysuccinimide.

1–Hydeoxy–1,2,3–triazole–4–carboxylate.

Iodine Monobromide.

Iodine Monochloride.

p–Iodobenzyl Bromide.

Iodonium Di–sym–collidine Perchlorate.

Iodonium Di–sym–collidine Trifluoromethanesulfonate.

2–(2–Iodopheny)ethanethiol.

N–Iodosaccharin.

N–Iodosuccinimide.

Isobutyl Chloroformate.

Isopropenyl Chloroformate.

Levulinic Anhydride.

6–Mercapto–4–dibenzofuranol.

Mercuric Bromide.

Mercuric Cyanide.

Mesitylenesulfonyl Chloride.

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

Mesitylsulfonyl–1H–1,2,4–Triazole.

p–Methoxybenzyl Chloride.

Methoxyphenyl Benzenethiosulfinate(MPBT).

1–(4–Methoxyphenyl)–2–(4′–methylbenzylthio)ethylamme.

2–Methoxypropene.

4–Methoxytriphenylmethyl chloride.

N–Methylcarbazole.

Methyl Trifluoromethanesulfonate.

2–Methyl–1–)1–methylethyl)propyl.

Chloroformate (doc–Cl).

N–Methylmorpholine.

N–Methylmorpholine Polystyrene (PS–NMM).

2–Methylsulfonyl–3–phenyl–prop–2–enyl Chloroformate.

5–Methylthio–1H–tetrazole.

2–Naphthylmethyl Bromide.

p–Nitrobenzenesulfonyl–4–nitroimidazole.

o–Nitrobenzyl Bromide.

p–Nitrobenzyl Bromide.

p–Nitrophenol.

5–(4–Nitrophenyl)–1H–Tetrazole.

Nitrosonium Tetrafluoroborate.

2–(5–Norbornene–2,3–dicarboxamido)–1,1,3,3–Tetramethyluronium Tetrafluoroborate.

Octenediol.

S–(1–Oxido–2–pyridinyl)–1,1,3,3–Tetramethylthiouronium Hexafluorophosphate (HOTT).

Pentafluorophenol.

Pentafluorophenyl Diphenylphosphinate (FDPP).

4–Pentenoic Acid.

4–Pentenol.

Phenyl–Bis(thiophenyl)sulfonium Hexachloroantimonate.

Phenyl Chlorothionocarbonate.

1,2–Phenylene Phosphorochloridate.

Phenyl N–Phenylphosphoramidochloridate.

Phenyl Phosphorodi(1–imidazolate).

2–(Phenylseleno)–1H–isoindole–1,3(2H)–dione.

(2–Phenylsulfonyl)ethoxy Dichlorophosphine.

2–Phenylthioethanol.

N–Phenyltrifluoroacetimidoyl Chloride.

Phosphorus Oxychloride.

Phthalic Anhydride.

Polyhexamethylenecarbodiimide.

Polystyrene–bound Dimethylaminopyridine (PS–DMAP).

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

Polymer–bound N–Hydroxysuccimimide.

Polystyrene–1–ethyl–3–(3′–dimethylaminopropyl)–carbodiimide Hydrochloride (PS–EDCI).

Polystyrylooronic Acid.

Potassium ethyl Xanthate.

N–[(Propargyloxycarbonyl)oxy]maleimide–styrene

Copolymer (Proc–resin).

Pyridine–2–thiol.

H–Pyrophosphonic Acid.

Silver Oxide.

Silver Salicylate.

Silver Silicate.

Silver(I) Tetrafluoroborate.

Silver Trifluoromethanesulfonate.

O–(N–Succinimidyl)–1,1,3,3–tetramethyluronium.

Tetrafluoroborate (TSTU).

9–(2–Sulfo)fluorenylmethyloxycarbonyl Chloride.

Tetrachlorophthalic Anhydride.

Tetrachlorophthalimide.

Tetraethyl Pyrophosphate.

3,3′,4,4′–Tetrahydro–6,6′–bi(2H–pyran).

1,1,2,2–Tetramethoxycyclohexane.

Tetramethylfluoroformamidinium Hexafluorophosphate.

Tetramethylurea.

1H–Tetrazole.

1,1′–Thiocaronyldiimidazole.

1,1′–Thionylimidazole.

2–Thiopyridyl chloroformate.

Tin (IV) Chloride.

Tin(II) Chloride–Silver(I) Perchlorate.

Tin(II) Trifluoromethanesulfonate.

p–Tolydiphenylmethyl Chloride.

1,2,4–Triazole.

Tri–t–butypyridine.

Trichloroacetonitrile.

Triethylsily Trifluoromethanesulfonate.

Trifluoromethanesulfonic Anhydride.

m–Trifluoromethylbenzoyl Chloride.

Trimethylphosphine.

Trimethylsily Trifluoromethanesulfonate.

Triphenylcarbenium Tetrafluoroborate.

Triphenylchloromethane.

Triphenylmethyl Perchlorate.

Triphenylphosphine–N–Bromosuccinimide.

Triphenylphosphine Carbon Tetrabromide.

Triphenylphosphine Carbon Tetrachloride.

Triphenylphosphine Dibromide.

Triphenylphosphine Diethylazodicarboxylate.

Triphenylphosphine Hydrobromide.

Triphenylphosphine Selenide.

Tris(dimethylamino)phosphine Carbon Tetrabromide.

Trity Tetrakis (pentafluorophenyl)borate.

Zinc Bromide.

Zinc Chloride.

List of Contributors.

Reagent Formula Index.

Subject Index.

O autorze

David Crich was born in 1959; BSc, Surrey University, 1981; DEsSc, University of Paris, 1984; Postdoctoral Fellow, Institut de Chimie des Substances Naturelles, 1984–1985; Lecturer, University College, London, 1985–1990; Laureat of the Academy of Sciences (France) 1989; Corday Morgan Medal (Royal Society of Chemistry), 1990; University of Illinois Scholar, 1992; Visiting Professor, University of Aix–Marseille, 1992: Fellow of the A. P. Sloan Foundation, 1994–1996; Tate and Lyle Carbohydrate Chemistry Medal (Royal Society of Chemistry), 1995. Since1997 Distinguished Professor of Organic Chemistry at the University of Illinois at Chicago. Since 2001 on the Editorial Board of e–EROS.

Blurb

The Synthesis of biopolymers and their conjugates is of ever increasing importance in bioorganic chemistry and chemical biology. As the need for such systems becomes ever more widespread, their synthesis is necessarily practiced in a broader spectrum of laboratories beyond the specialized ones that have traditionally concentrated in the area. For each type of biopolymer there exists a wide array of protecting systems and coupling reagents from which the practitioner must make and informed choice. This Handbook presents short, informative articles on approximately 250 of the most widely used reagents in the area in a single, affordable volume so as to facilitate the task of the experimentalist. Each of the articles, drawn from the e–EROS database, is written by an experienced worker in the area and collects together a summary of the most pertinent reactions for every reagent with references to the original literature. Each article also contains an overview of the physical properties of the reagent, conditions for its storage, and purification methods. This Handbook will prove of highest value to virtually everybody working in organic synthesis, medicinal chemistry or natural product chemistry.

All the information compiled in this volume is also available in electronic format on Wiley InterScience. The electronic Encyclopedia of Reagents for Organic Synthesis (e–EROS) includes all the reagents described in this volume plus many more reagents of other types and for other uses. e–EROS allows for both text and structure searches and has many new and updated entries added every year.
For more information visit:
http://www.mrw.interscience.wiley.com/eros/