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1、 2000 Toby Broom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.co.uk Abbreviation Full Name Some Uses Structures Ac Acetyl Very common protecting group for alcohols and phenols R O Ad Adamantyl Protecting group for acids, thiols a
2、nd alcohols R AD Asymmetric dihydroxylation OHHO N H N O H O O Cl OsO4+NMO+ AE Asymmetric epoxidation Sharpless Conditions OHO OH H CO2Et OH EtO2C HO H tBuOOH +Ti(OiPr)4+ AIBN ? ,? -Azoisobutyronitrile Makes radicals NCN NCN Aldrithiol 2,2-Dipyridyldisulphide Thiolating Reagent NSSN All Allyl Protec
3、ting group for phenols, acids and alcohols especially carbohydrates R Alloc Allyloxycarbonyl Protecting group for alcohols, amines O O R 9-BBN 9-Borabicyclononane Hindered reductant BBN BH BMS Borane-methylsulphide complex Reducing agent BH3SMe2 BINAP 2,2-Bis(diphenylphosphino)-1,1- binapthyl Ligand
4、 for Ru catalytic hydrogenation and Buchwald reaction PPh2 PPh2 BINAPO Phosphinous acid, diphenyl-1,1- binapthalene-2-2-diyl ester Ligand for Ru catalytic hydrogenation OPPh2 OPPh2 Boc tert-Butoxycarbonyl Protecting group for amines especially peptides O OR BOM Benzyloxymethyl Protecting group for a
5、lcohols, phenols, acids and amines O R BOP Benzotriazol-1- yloxytris(dimethylamino)phosphon ium hexafluorophospate Peptide coupling reagent N N N P N NN PF6 2000 Toby Broom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.co.uk BOP-C
6、l Bis(2-oxo-3- oxazolidinyl)phosphinic chloride Peptide coupling reagent O N P N Cl O O OO Bn Benzyl Protecting group for alcohols, phenols, acids, amides, amines and carbonyls R Br Brosylate, Bromobenzenesulphonyl Activating group for alcohols BrS O O R BTAF Benzyltrimethylammonium fluoride Fluorat
7、ing reagent NF Bum t-butoxymethyl Protecting group for amines, alcohols OR Bz Benzoyl Protecting group for thiols, alcohols, phenols much more stable than acetate OR BHT tert-Butylhydroxytoluene Stablizer for ethers OH CAN Ceric ammonium nitrate Oxidising agent (NH4)2Ce(NO2)6 CBS Corey-Bashki-Shibat
8、 Chiral reducing agent for carbonyls N O B Ph Ph H BH3 + Cbz or Z Benzyloxycarbonyl Very common protecting group for amines especially in amino acids O R O COD Cyclooctadiene Ligand for transition metal catalysts and used to make 9-BBN Cp Cyclopentadienyl As it s anion a ligand for transition metals
9、 and a common Diels-Alder Diene mCPBA meta-chloroperoxybenzoic acid Oxidising agent used for making epoxides and Baeyer-Villiger reaction O O OH Cl 18-Crown-6 (18C6) 1,4,7,10,13,16- hexaoxocyclooctadecane Phase transfer catalyst O O O OO O CSA Camphorsulphonic acid Chiral resolving agent O HO3SH2C C
10、ys Cystine Amino acid NH2 O OHHS 2000 Toby Broom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.co.uk Dabco 1,4-Diazabicyclo2.2.2octane Strong hindered base N N DAST Diethylaminosuphur trifluoride Fluorinating agent N S F F F dba D
11、ibenzylideneacetone Z,Z-1,5-diphenyl-1,4-pentadien-3- one Ligand for palladium O DBN 1,5-Diazabicycolo4.3.0non-5- ene Strong hindered base N N DBU 1,8-Diazabicyclo5.4.0undec-7- ene Strong hindered base N N DCC 1,3-Dicyclohexylcarbodiimide Peptide coupling reagent NC N DDQ 2,3-Dichloro-5,6-dicyano-1,
12、4- benzoquinone Oxidant O O Cl Cl CN CN DEAD Diethyl azodicarboxylate Reagent used in Mitsunobu Reaction (inversion of alcohols) N O N O DHP Dihydropyran The reagent used to make THP protected alcohols, acids and phenols. O DHQD Dihydroquinidine Chiral ligand N H N O H HO DIAD Diisopropyl azodicarbo
13、xylate Reagent used in Mitsunobu Reaction (inversion of alcohols) NN OO DIBAL DIBAL-H Diisobutylaluminium hydride Reducing agent for the selective reduction of ester to aldehydes AlH DIC Diisopropylcardodiimide Peptide coupling reagent CNN DIPEA DIEA Diisopropylethylamine Proton sponge, base N DMD D
14、imethyldioxorane Used for making epoxides OO DMAP 4-Dimethylaminopyridine Weak base NN DME Dimethoxyethane Solvent O O DMF N,N-Dimethylformamide Solvent O N 2000 Toby Broom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.co.uk DMP D
15、ess-Martin periodate From Iodobenzoic acid heat with AcOH then AcO2 Mild oxidizing agent for alcohols to aldehydes I O O AcO OAc OAc DMPM 3,4-Dimethoxybenzyl Protecting group for alcohols (can be removed in presence of MPM selectively) R O O DMPU 1,3-Dimethyl-3,4,5,6-tetrahydro- 2(1H)-pyrimidinone N
16、on carcinogenic replacement for HMPA N NO DMS Dimethylsulphide Used for quenching Ozonolysis and ligand for BH3 S DMSO Dimethylsulphoxide Solvent and oxidant S O DPPA Diphenylphosphoryl azide Organic Source of Azide O P O O N N N EDCI 1-ethyl-3-3- (dimethylamino)propyl carbodiimide Reagent used in Mitsunobu Reaction (inversion of alcohols) C N N N EDTA Ethylenediamminetetraacetic acid Chelating agent for metal ions. N NO OH O HO HO O O OH EE 1-Ethoxyethyl Pro
