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 OAd Adamantyl Protecting group for acids, thiols an
2、d alcohols RAD Asymmetric dihydroxylation OH HON H N O H O O Cl OsO 4 + NMO +AE Asymmetric epoxidation Sharpless Conditions OH O OHH CO 2 Et OH EtO 2 C HO H t BuOOH + Ti(O i Pr) 4 +AIBN ?,?-Azoisobutyronitrile Makes radicals NC N N CNAldrithiol 2,2-Dipyridyldisulphide Thiolating Reagent N SS NAll Al
3、lyl Protecting group for phenols, acids and alcohols especially carbohydrates RAlloc Allyloxycarbonyl Protecting group for alcohols, amines O O R9-BBN 9-Borabicyclononane Hindered reductant BBNB HBMS Borane-methylsulphide complex Reducing agent BH 3 SMe 2BINAP 2,2-Bis(diphenylphosphino)-1,1- binapth
4、yl Ligand for Ru catalytic hydrogenation and Buchwald reaction PPh 2 PPh 2BINAPO Phosphinous acid, diphenyl-1,1- binapthalene-2-2-diyl ester Ligand for Ru catalytic hydrogenation OPPh 2 OPPh 2Boc tert-Butoxycarbonyl Protecting group for amines especially peptidesO O RBOM Benzyloxymethyl Protecting g
5、roup for alcohols, phenols, acids and amines O RBOP Benzotriazol-1- yloxytris(dimethylamino)phosphon ium hexafluorophospate Peptide coupling reagent N N N P N N N PF 6 2000 Toby Broom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.
6、co.uk BOP-Cl Bis(2-oxo-3- oxazolidinyl)phosphinic chloride Peptide coupling reagent O N P N Cl O O O OBn Benzyl Protecting group for alcohols, phenols, acids, amides, amines and carbonyls RBr Brosylate, Bromobenzenesulphonyl Activating group for alcohols Br S O O RBTAF Benzyltrimethylammonium fluori
7、de Fluorating reagent N FBum t-butoxymethyl Protecting group for amines, alcohols O RBz Benzoyl Protecting group for thiols, alcohols, phenols much more stable than acetate O RBHT tert-Butylhydroxytoluene Stablizer for ethers OHCAN Ceric ammonium nitrate Oxidising agent (NH 4 ) 2 Ce(NO 2 ) 6 CBS Cor
8、ey-Bashki-Shibat Chiral reducing agent for carbonyls N O B Ph Ph H BH 3 +Cbz or Z Benzyloxycarbonyl Very common protecting group for amines especially in amino acids O R OCOD Cyclooctadiene Ligand for transition metal catalysts and used to make 9-BBN Cp Cyclopentadienyl As its anion a ligand for tra
9、nsition metals and a common Diels-Alder Diene mCPBA meta-chloroperoxybenzoic acid Oxidising agent used for making epoxides and Baeyer-Villiger reaction O O OH Cl18-Crown-6 (18C6) 1,4,7,10,13,16- hexaoxocyclooctadecane Phase transfer catalyst O O O O O OCSA Camphorsulphonic acid Chiral resolving agen
10、t O HO 3 SH 2 CCys Cystine Amino acid NH 2 O OH HS 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 NDAST Diethylaminosuphur trifluoride Fluorinating agen
11、t N S F F Fdba Dibenzylideneacetone Z,Z-1,5-diphenyl-1,4-pentadien-3- one Ligand for palladium ODBN 1,5-Diazabicycolo4.3.0non-5- ene Strong hindered base N NDBU 1,8-Diazabicyclo5.4.0undec-7- ene Strong hindered base N NDCC 1,3-Dicyclohexylcarbodiimide Peptide coupling reagent N C NDDQ 2,3-Dichloro-5
12、,6-dicyano-1,4- benzoquinone Oxidant O O Cl Cl CN CNDEAD Diethyl azodicarboxylate Reagent used in Mitsunobu Reaction (inversion of alcohols) N O N ODHP Dihydropyran The reagent used to make THP protected alcohols, acids and phenols. ODHQD Dihydroquinidine Chiral ligand N H N O H HODIAD Diisopropyl a
13、zodicarboxylate Reagent used in Mitsunobu Reaction (inversion of alcohols) N N O ODIBAL DIBAL-H Diisobutylaluminium hydride Reducing agent for the selective reduction of ester to aldehydes Al HDIC Diisopropylcardodiimide Peptide coupling reagent C N NDIPEA DIEA Diisopropylethylamine Proton sponge, b
14、ase NDMD Dimethyldioxorane Used for making epoxides O ODMAP 4-Dimethylaminopyridine Weak base N NDME Dimethoxyethane Solvent O ODMF 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
15、.uk DMP Dess-Martin periodate From Iodobenzoic acid heat with AcOH then AcO 2Mild oxidizing agent for alcohols to aldehydes I O O AcO OAc OAcDMPM 3,4-Dimethoxybenzyl Protecting group for alcohols (can be removed in presence of MPM selectively) R O ODMPU 1,3-Dimethyl-3,4,5,6-tetrahydro- 2(1H)-pyrimid
16、inone Non carcinogenic replacement for HMPA N N ODMS Dimethylsulphide Used for quenching Ozonolysis and ligand for BH 3SDMSO Dimethylsulphoxide Solvent and oxidant S ODPPA Diphenylphosphoryl azide Organic Source of Azide O P O O N N NEDCI 1-ethyl-3-3- (dimethylamino)propyl carbodiimide Reagent used
17、in Mitsunobu Reaction (inversion of alcohols) C N N NEDTA Ethylenediamminetetraacetic acid Chelating agent for metal ions. N N O OH O HO HO O O OHEE 1-Ethoxyethyl Protecting group for amines and alcohols O RFDPP Pentafluorophenyl diphenylphosphinate Peptide coupling reagent P O Ph Ph F F F F FFmoc 9
18、-Fluorenylmethoxycarbonyl Protecting group for amines, alcohols and acids (very stable to acids) O O RHATU O-(7-azabenzotrizol-1-yl)-1,1,3,3, tetramethyluronium hexafluorophosphate N-(dimethylamino)-1H-1, 2, 3- triazol 4, 5-b pyridiylmethylene- N-methylmethanaminium hexafluorophosphate N-oxide Pepti
19、de coupling agent N N N N N N O PF 6HMPA Hexamethylphosphoramde Co-solvent O P N N NHMPT Hexamethylphorous triamide Co-solvent P N N N 2000 Toby Broom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.co.uk HOBt 1-hydroxbenzotriazole
20、Peptide coupling agent N N N OHIm Imidazole Base used in silylations N N HIpc Isopinocampheyl Chiral ligand usually attached to boron for asymmetric hydroborations RKDA Potassium diisopropylamide Non-Nucelophillic Base N KKHMDS Potassium bis(trimethylsilyl)amide Non-Nucelophillic Base K Si N SiK-Sel
21、ectride Potassium tri-sec- butylborohydride Stereoselective reductant via chelation control K B HLDA Lithium diisopropylamide Non-Nucelophillic Base N LiLDEA Lithium diethylamide Strong Base N LiLiHMDS Lithium bis(trimethylsilyl)amide Non-Nucelophillic Base Si N Si LiMEM 2-Methoxyethoxymethyl Protec
22、ting group for alcohols and phenols (more stable than MOM) O O RMOM Methoxymethyl Protecting group for alcohols and phenols O RMoz or MeOZ p-Methoxybenzyl carbonyl Protecting group for amines O O O R 2 NMPM p-Methoxybenzyl Protecting group for alcohols and phenols (more easily oxidativly cleaved) R
23、O3,4,5 MS Molecular sieves Beads for absorbing typically water Ms Methanesulphonyl Activating group alcohols S R O OMSA Methanesulfonic acid Very strong organic acid S OH O OMW Microwave Energy source for reactions NaHMDS Sodium bis(trimethylsilyl)amide Non-Nucelophillic Base Si N Si Na 2000 Toby Br
24、oom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.co.uk NBS N-Bromosuccinimide Radical Brominating agent N O O BrNIS N-Iodosuccinimide Radical Iodinating agent N O O INMM N-Methylmorpholine Base O NNMO N-Methylmorpholine-N-oxide C
25、o-Oxidant O N ON-PSP N-Phenylselenophtalimide Electrophillic source of phenyl selanide N O O SeNps o-Nitrophenylsulphonyl Protecting group for amines (easer to cleave than Ts) S O O R NO 2Oxone Potassium peroxoymonosulfate Oxidant 2KHSO 5. KHSO 4. K 2 SO 4PDC Pyridinium dichromate Oxidant for alcoho
26、ls to aldehydes and ketones N H 2 Cr 2 O 7 2-PCC Pyridinium chlorochromate Oxidant for alcohols to aldehydes and ketones N H ClCrO 3 -Ph Phenyl Protecting group for acids, thiols RPiv Pv Pivaloyl Protecting group for alcohols and phenols O ORPMB p-Methoxybenzyl Protecting group for amines, amides, a
27、lcohols, phenols and acids R OPMP p-Methoxyphenyl Protecting group for alcohols O RPPA Polyphosphoric acid Strong dehydrating agent P O O HO HO xPPTS Pyridinium p-toluenesulphoate Very weak acid, used to add an exact amount of acid as its a solid S O O O HNPTSA p-TsOH p-Toluenesulphonic acidStrong o
28、rganic acidS O O OHPy Pyridine Weak organic base N 2000 Toby Broom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.co.uk PyBroP Bromotripyrrolidinophosphonium hexafluorophosphate Peptide coupling reagent N P N N Br F 6 PSEM 2-(trime
29、thylsilyl)ethoxymethyl Protecting group for amines, alcohols, phenols, acids Si RSEMCl 2-(trimethylsilyl)ethoxymethyl chloride The reagent used to provide the above protection Si O ClRed-Al Sodium bis(2- methoxyethoxy)aluminium hydride Versatile Reductant (more soluble at low temperatures) Al O O O
30、O H H NaTBAF Tetrabutylammonium fluoride Fluorinating agent Bu 4 N FTBDMS tert-Butyldimethylsilyl Very popular protecting group for alcohols, phenols, thiols and amines (1000x more stable than TMS) Si RTBDPS tert-Butyldiphenylsilyl Protecting group for alcohols and amines (100x more stable than TBDM
31、S) Si RTBS tert-Butylmethylsilyl Very popular protecting group for alcohols, phenols, thiols and amines (1000x more stable than TMS) Si RTBTU O-Benzotriazol-1-yl-N,N,N,N- tetramethyluronium tetrafluoroborate Peptide coupling reagent N N N O N N B F F F FTCDI Thiocarbonyl diimidazole Used in radical
32、decarboxylation S N N N NTEA Triethylamide Base NTEMPO 2,2,6,6-tetramethyl-1- piperdinyloxy free radical Stable radical oxidant and initiator N OTf Trifluoromethanesulphonyl Triflate Activating agent for alcohols and phenols in Palladium catalysed couplings. Also protecting group for amines S O O F
33、F F RTFA Trifluoroacetic acid/ Trifluoroacetyl Very strong organic acid used in solid phase synthesis for cleaving from resin and used to remove many protecting groups O OH F F FTFAA Trifluoroacetic anhydride Used to make protected amines and alcohols (very easily cleaved, see TFA) F 3 C O O O F 3 C
34、 2000 Toby Broom No part of this document may be reproduced or modified without the express permission of Toby Broom. tbroomtotalise.co.uk THP Tetrahydropyran Protecting group for alcohols, acids and phenols Prepared from DHP O ORTIPS Triisopropylsilyl Protecting group for alcohols and amines (stabi
35、lity between TBDMS and TBDPS) Si RTMG Tetramethylguanidine Base N N NHTMS Trimethylsilyl Protecting group for alcohols, amines, amino acids, acids, phenols and thiols (probably the most common protecting group) Si RTMSCl Trimethylsilyl chloride One of the reagent used to provide the above protection
36、 Si ClTMSOTf Trimethylsilyl trifluoromethanesulfonate Lewis Acid, typically used for making silylenol ethers S O O F F F SiTol p-Toluyl Protecting group for acids, thiols Ro-Tolyl o-Toluyl Protecting group for acids, thiols RTPAP Tetra-n-propylammonium perruthenate Oxidant Pr 4 N RuO 4Tr Trityl Prot
37、ecting group for amines, alcohols, amides and thiols C RTroc 2,2,2-Trichlorethoxycarbonyl Protecting group for thiols, phenols O Cl Cl Cl O RTs p-Toluenesulphonyl, Tosyl Activating group for alcohols and protecting group for amines S O O RVitride Sodium bis(2- methoxyethoxy)aluminum hydride Versatile Reductant (more soluble at low temperatures) Al O O O O H H NaZ or Cbz Benzyloxycarbonyl Very common protecting group for amines especially in amino acids O O R
