基团试剂的英文简称全称结构及用途

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Abbreviation Full Name Ac Ad Acetyl Adamantyl Some Uses Very common protecting group for alcohols and phenols Protecting group for acids, thiols and alcohols HOOHStructures ORR AD Asymmetric dihydroxylation OOsO4+NMO+OHONHN Cl AE Asymmetric epoxidation Sharpless Conditions OHOOHtBuOOH+Ti(OiPr)4+EtO2CHOHCO2EtHOHAIBN Aldrithiol® All ?,?'-Azoisobutyronitrile 2,2'-Dipyridyldisulphide Allyl Makes radicals Thiolating Reagent NCNNCN NSSNAlloc 9-BBN Allyloxycarbonyl 9-Borabicyclononane Protecting group for phenols, acids and alcohols especially carbohydrates Protecting group for alcohols, amines Hindered reductant BBN R ROO HBBMS BINAP Borane-methylsulphide complex 2,2'-Bis(diphenylphosphino)-1,1'-binapthyl Reducing agent Ligand for Ru catalytic hydrogenation and Buchwald reaction BH3SMe2 PPh2PPh2BINAPO Phosphinous acid, diphenyl-[1,1'-binapthalene]-2-2'-diyl ester Ligand for Ru catalytic hydrogenation OPPh2OPPh2Boc BOM tert-Butoxycarbonyl Benzyloxymethyl Protecting group for amines especially peptides Protecting group for alcohols, phenols, acids and amines Peptide coupling reagent ORO ROBOP Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophospate NNPNNNNPF6 © 2000 Toby Broom

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BOP-Cl Bis(2-oxo-3-oxazolidinyl)phosphinic chloride Benzyl Peptide coupling reagent OONPNClOOROBn Br BTAF Brosylate, Bromobenzenesulphonyl Benzyltrimethylammonium fluoride Protecting group for alcohols, phenols, acids, amides, amines and carbonyls Activating group for alcohols Fluorating reagent OBrSRONF Bum Bz t-butoxymethyl Benzoyl BHT tert-Butylhydroxytoluene Protecting group for amines, alcohols Protecting group for thiols, alcohols, phenols much more stable than acetate Stablizer for ethers RO OR OHCAN CBS Ceric ammonium nitrate Corey-Bashki-Shibat Oxidising agent Chiral reducing agent for carbonyls (NH4)2[Ce(NO2)6] PhPhNOBH+BH3Cbz or Z Benzyloxycarbonyl COD Cp mCPBA Cyclooctadiene Cyclopentadienyl meta-chloroperoxybenzoic acid Very common protecting group for amines especially in amino acids Ligand for transition metal catalysts and used to make 9-BBN As it’s anion a ligand for transition metals and a common Diels-Alder Diene Oxidising agent used for making epoxides and Baeyer-Villiger reaction Cl ROO OOOH18-Crown-6 (18C6) 1,4,7,10,13,16-hexaoxocyclooctadecane Phase transfer catalyst OO OOOOCSA Camphorsulphonic acid Chiral resolving agent HO3SH2C OOCys Cystine Amino acid HS OHNH2 © 2000 Toby Broom

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Dabco™ DAST 1,4-Diazabicyclo[2.2.2]octane Diethylaminosuphur trifluoride Strong hindered base Fluorinating agent FFFSNN Ndba DBN DBU DCC DDQ Dibenzylideneacetone Z,Z-1,5-diphenyl-1,4-pentadien-3-one 1,5-Diazabicycolo[4.3.0]non-5-ene 1,8-Diazabicyclo[5.4.0]undec-7-ene 1,3-Dicyclohexylcarbodiimide 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Ligand for palladium O Strong hindered base Strong hindered base Peptide coupling reagent Oxidant ClClONN CNCNNNNCNODEAD DHP DHQD Diethyl azodicarboxylate Dihydropyran Dihydroquinidine Reagent used in Mitsunobu Reaction (inversion of alcohols) The reagent used to make THP protected alcohols, acids and phenols. Chiral ligand OONN O NHHOHONDIAD Diisopropyl azodicarboxylate Reagent used in Mitsunobu Reaction (inversion of alcohols) Reducing agent for the selective reduction of ester to aldehydes Peptide coupling reagent Proton sponge, base OONNDIBAL DIBAL-H DIC DIPEA DIEA DMD DMAP DME DMF Diisobutylaluminium hydride HAlDiisopropylcardodiimide Diisopropylethylamine NCN NDimethyldioxorane 4-Dimethylaminopyridine Dimethoxyethane N,N-Dimethylformamide Used for making epoxides Weak base Solvent Solvent N OO N OO NO © 2000 Toby Broom

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DMP Dess-Martin periodate From Iodobenzoic acid heat with AcOH then AcO2 3,4-Dimethoxybenzyl Mild oxidizing agent for alcohols to aldehydes OAcOOAcIOAcODMPM DMPU 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone Dimethylsulphide Dimethylsulphoxide Diphenylphosphoryl azide Protecting group for alcohols (can be removed in presence of MPM selectively) Non carcinogenic replacement for HMPA Used for quenching Ozonolysis and ligand for BH3 Solvent and oxidant Organic Source of Azide OORNON DMS DMSO DPPA S OSOPONNNOEDCI EDTA 1-ethyl-3-[3-(dimethylamino)propyl] carbodiimide Ethylenediamminetetraacetic acid Reagent used in Mitsunobu Reaction (inversion of alcohols) Chelating agent for metal ions. HO NNCN OONHOOOHNOOHEE FDPP 1-Ethoxyethyl Pentafluorophenyl diphenylphosphinate Protecting group for amines and alcohols Peptide coupling reagent RO FFFFOPhPPhFFmoc 9-Fluorenylmethoxycarbonyl Protecting group for amines, alcohols and acids (very stable to acids) O ROHATU HMPA 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 Hexamethylphosphoramde Peptide coupling agent N ONNNNN PF6 Co-solvent ONPNNHMPT Hexamethylphorous triamide Co-solvent N NPN © 2000 Toby Broom

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HOBt 1-hydroxbenzotriazole Peptide coupling agent NNNOHIm Imidazole Base used in silylations NNHIpc Isopinocampheyl KDA Potassium diisopropylamide Chiral ligand usually attached to boron for asymmetric hydroborations Non-Nucelophillic Base NK R KHMDS Potassium bis(trimethylsilyl)amide Non-Nucelophillic Base NSiSiKK-Selectride® Potassium tri-sec-butylborohydride Stereoselective reductant via chelation control BHK LDA Lithium diisopropylamide Non-Nucelophillic Base NLi LDEA Lithium diethylamide Strong Base NLiLiHMDS Lithium bis(trimethylsilyl)amide Non-Nucelophillic Base NSiSiLiMEM MOM Moz or MeOZ 2-Methoxyethoxymethyl Methoxymethyl p-Methoxybenzyl carbonyl Protecting group for alcohols and phenols (more stable than MOM) Protecting group for alcohols and phenols Protecting group for amines ORO OR OR2NOOMPM 3,4,5Å MS Ms MSA MW NaHMDS p-Methoxybenzyl Molecular sieves Methanesulphonyl Methanesulfonic acid Microwave Sodium bis(trimethylsilyl)amide Protecting group for alcohols and phenols (more easily oxidativly cleaved) Beads for absorbing typically water Activating group alcohols Very strong organic acid Energy source for reactions Non-Nucelophillic Base OR OSROOSOHO SiSiNNa © 2000 Toby Broom

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NBS N-Bromosuccinimide Radical Brominating agent ONBrONIS N-Iodosuccinimide Radical Iodinating agent IONONMM NMO N-PSP N-Methylmorpholine N-Methylmorpholine-N-oxide N-Phenylselenophtalimide Base Co-Oxidant Electrophillic source of phenyl selanide NOO ON ONSeONps o-Nitrophenylsulphonyl Protecting group for amines (easer to cleave than Ts) Oxidant Oxidant for alcohols to aldehydes and ketones NH. OSRONO2Oxone® PDC Potassium peroxoymonosulfate Pyridinium dichromate . 2KHSO5 KHSO4 K2SO4 Cr2O72-2PCC Pyridinium chlorochromate Oxidant for alcohols to aldehydes and ketones Protecting group for acids, thiols Protecting group for alcohols and phenols Protecting group for amines, amides, alcohols, phenols and acids Protecting group for alcohols Strong dehydrating agent NHClCrO3-Ph Piv Pv PMB PMP PPA Phenyl Pivaloyl R OORp-Methoxybenzyl p-Methoxyphenyl Polyphosphoric acid OR OR OHOPOHOxPPTS Pyridinium p-toluenesulphoate PTSA p-TsOH Py p-Toluenesulphonic acid Pyridine Very weak acid, used to add an exact amount of acid as it’s a solid Strong organic acid Weak organic base OSOOHN OSOHON © 2000 Toby Broom

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PyBroP Bromotripyrrolidinophosphonium hexafluorophosphate Peptide coupling reagent NBrPNF6PNSEM SEMCl [2-(trimethylsilyl)ethoxy]methyl Red-Al® Protecting group for amines, alcohols, phenols, acids [2-(trimethylsilyl)ethoxy]methyl The reagent used to chloride provide the above protection Sodium bis(2-Versatile Reductant (more methoxyethoxy)aluminium hydride soluble at low temperatures) O RSi ClOSi OOOAlHHNaBu4NFTBAF TBDMS Tetrabutylammonium fluoride tert-Butyldimethylsilyl Fluorinating agent Very popular protecting group for alcohols, phenols, thiols and amines (1000x more stable than TMS) Protecting group for alcohols and amines (100x more stable than TBDMS) Very popular protecting group for alcohols, phenols, thiols and amines (1000x more stable than TMS) Peptide coupling reagent NN SiRTBDPS tert-Butyldiphenylsilyl SiRSiRTBS tert-Butylmethylsilyl TBTU O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate Thiocarbonyl diimidazole NNONSNNNFBFFFTCDI Used in radical decarboxylation Base NTEA TEMPO Triethylamide 2,2,6,6-tetramethyl-1-piperdinyloxy free radical Trifluoromethanesulphonyl Triflate Trifluoroacetic acid/ Trifluoroacetyl NStable radical oxidant and initiator Activating agent for alcohols and phenols in Palladium catalysed couplings. Also protecting group for amines Very strong organic acid used in solid phase synthesis for cleaving from resin and used to remove many protecting groups Used to make protected amines and alcohols (very easily cleaved, see TFA) NOTf OSRFFFO TFA FFFOOH TFAA Trifluoroacetic anhydride OF3COF3CO © 2000 Toby Broom

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THP Tetrahydropyran TIPS Triisopropylsilyl TMG Tetramethylguanidine Protecting group for alcohols, acids and phenols Prepared from DHP Protecting group for alcohols and amines (stability between TBDMS and TBDPS) Base NOOR SiR NHNTMS Trimethylsilyl TMSCl TMSOTf Trimethylsilyl chloride Trimethylsilyl trifluoromethanesulfonate p-Toluyl o-Toluyl Tetra-n-propylammonium perruthenate Trityl Protecting group for alcohols, amines, amino acids, acids, phenols and thiols (probably the most common protecting group) One of the reagent used to provide the above protection Lewis Acid, typically used for making silylenol ethers Protecting group for acids, thiols Protecting group for acids, thiols Oxidant Protecting group for amines, alcohols, amides and thiols SiR SiCl FFFOSSiORTol o-Tolyl TPAP Tr R Pr4NRuO4 CRTroc Ts Vitride® 2,2,2-Trichlorethoxycarbonyl p-Toluenesulphonyl, Tosyl Protecting group for thiols, phenols ClClOClROSROOOActivating group for alcohols and protecting group for amines Sodium bis(2-Versatile Reductant (more methoxyethoxy)aluminum hydride soluble at low temperatures) O OOAlHHNaZ or Cbz Benzyloxycarbonyl Very common protecting group for amines especially in amino acids ORO