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Issue 18, 2001
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Protecting groups

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Abstract

Covering: the literature published in 2000. Previous review: J. Chem. Soc., Perkin Trans. 1, 2000, 2495.

Abbreviations for reactions, reagents and protecting groups: 4 Å MS, molecular sieves, 4 Å; 9-BBN, 9-borabicyclo[3.3.1]nonane; 4-QUI, 4-quinolylmethyl; Ac, acetyl; Acm, acetamidomethyl; All, allyl; Aloc, allyloxycarbonyl; BCB, B-bromocatecholborane; bipy, 2,2′-bipyridyl; Bn, benzyl; BOB, 4-benzyloxybutyryl; BOBCl, bis(2-oxooxazolidin-3-yl)phosphinic chloride; BOBOH, benzyloxybutyric acid; Boc, tert-butoxycarbonyl; Bz, benzoyl; CAN, ceric ammonium nitrate; CBB, catechol boron bromide; Cbz, benzyloxycarbonyl; CSA, camphorsulfonic acid; ClAc, chloroacetyl; ClAzb, 4-azido-3-chlorobenzyl; CNAP, 2-naphthylmethyl carbamate; CTFB, 4-trifluoromethylbenzyl carbamate; Cy, cyclohexyl; DABCO, 1,4-diazabicyclo[2.2.1]octane; dba, dibenzylideneacetone; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DCC, dicyclohexylcarbodiimide; DDQ, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; DEAD, diethyl azodicarboxylate; DIAD, diisopropyl azodicarboxylate; DIB, diacetoxyiodobenzene; DIBAL-H, diisobutylaluminium hydride; Dim, 2-(hydroxymethyl)-1,3-dithiane; DIPEA, diisopropylethylamine; DMAP, 4-dimethylaminopyridine; DME, 1,2-dimethoxyethane; DMF, dimethylformamide; DMPU, 1,3-dimethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one; DMSO, dimethyl sulfoxide; DMTr, 4,4′-dimethoxytrityl; DOPA, 3,4-dihydroxyphenylalanine; dppe, 1,2-bis(diphenylphosphino)ethane; EDC, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; Fmoc, fluoren-9-ylmethoxycarbonyl; Fmoc-OSu, N-(fluoren-9-ylmethoxycarbonyloxy)succinimide; HATU, N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate; HMPA, hexamethylphosphoramide; HOAt, 1-hydroxy-7-azabenzotriazole; HOBT, 1-hydroxybenzotriazole; MCPBA, m-chloroperbenzoic acid; MEM, 2-methoxyethoxymethyl; Mes, mesityl; MMTr, p-methoxyphenyldiphenylmethyl; MOM, methoxymethyl; MS, molecular sieves; Ms, methylsulfonyl; MsCl, methanesulfonyl chloride; NAP, 2-naphthylmethyl; NBS, N-bromosuccinimide; NCE, 2-[(1-naphthyl)carbamoyloxy]ethyl; NIS, N-iodosuccinimide; NMP, 1-methylpyrrolidin-2- one; Ns, 2-nitrobenzenesulfonamide; PBB, p-bromobenzyl; PCB, p-chlorobenzyl; PCC, pyridinium chlorochromate; Ph, phenyl; Pht, phthalimido; PMB, p-methoxybenzyl; PMBCl, p-methoxybenzyl chloride; PMBOTr, p-methoxybenzyl trityl ether; PMBOH, p-methoxybenzyl alcohol; PMP, p-methoxyphenyl; PSE, phenylsulfonylethylidene; Psoc, (2-phenyl-2-trimethylsilyl)ethoxycarbonyl; PTMSE, 2-phenyl-2-(trimethylsilyl)ethyl; Pv, pivaloyl; Pyr, pyridine; RCM, ring closing metathesis; SEM, 2-(trimethylsilyl)ethoxymethyl; Su, succinimide; TBAF, tetrabutylammonium fluoride; TBDPS, tert-butyldiphenylsilyl; TBS, tert-butyldimethylsilyl; TBTU, O-(benzotriazol-1-yl)-N,N,NN′-tetramethyluronium tetrafluoroborate; TDS, tris(2,6-diphenylbenzyl)silyl; Teoc, 2-trimethylsilylethoxycarbonyl; TES, triethylsilyl; Tf, trifluoromethylsulfonyl; TFA, trifluoroacetic acid; TfOH, trifluoromethanesulfonic acid; THF, tetrahydrofuran; THP, tetrahydropyranyl; Thr, threonine; TIPDS, 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl; TIPS, triisopropylsilyl; TMEDA, N,N,NN′-tetramethylethylenediamine; TMS, trimethylsilyl; TMSBr, bromotrimethylsilane; TMSCl, chlorotrimethylsilane; TMSE, 2-(trimethylsilyl)ethyl; TMSI, iodotrimethylsilane; TMSOTf, trimethylsilyl trifluoromethanesulfonate; Tr, trityl, (triphenylmethyl); Troc, 2,2,2-trichloroethoxycarbonyl; Ts, p-tolylsulfonyl; TsOH, toluene-p-sulfonic acid.

Graphical abstract: Protecting groups

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Article information


Submitted
11 Apr 2001
First published
29 Aug 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2109-2135
Article type
Review Article

Protecting groups

K. Jarowicki and P. Kocienski, J. Chem. Soc., Perkin Trans. 1, 2001, 2109
DOI: 10.1039/B103282H

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