Direct preparation of diacetals from 1,2-diketones and their use as 1,2-diol protecting groups

被引：84

作者：

Hense, A ^{[1
]}

Ley, SV ^{[1
]}

Osborn, HMI ^{[1
]}

Owen, DR ^{[1
]}

Poisson, JF ^{[1
]}

Warriner, SL ^{[1
]}

Wesson, KE ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,DEPT CHEM,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 14期

关键词：

D O I：

10.1039/a702497e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of 1,2-diketones have been evaluated as potential protecting groups for trans-1,2-diols pia 1,2-diacetal formation, The procedure is especially useful in oligosaccharide and natural product synthesis.

引用

页码：2023 / 2031

页数：9

共 17 条

[1] OXIDATION OF VICINAL DIOLS TO ALPHA-DICARBONYL COMPOUNDS BY TRIFLUOROACETIC-ANHYDRIDE ACTIVATED DIMETHYLSULFOXIDE [J].

AMON, CM ;

BANWELL, MG ;

GRAVATT, GL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4851-4855

[2] Transacetalization of diethyl tartrate with acetals of alpha-dicarbonyl compounds: A simple access to a new class of C-2-symmetric auxiliaries and ligands [J].

Berens, U ;

Leckel, D ;

Oepen, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) :8204-8208

[3] QUINONE STUDIES .I. EVIDENCE FOR NEW TYPE OF SUBSTITUTION REACTION OF PHENANTHRENE-9,10-QUINONE DERIVATIVES [J].

BHATT, MV .

TETRAHEDRON, 1964, 20 (04) :803-+

[4]

BOLS M, 1996, CARBOHYDRATE BUILDIN, P26

[5]

BUYCK LD, 1984, B SOC CHIM BELG, V93, P913

[6]

Douglas NL, 1996, SYNLETT, P793

[7] MILD AND EFFICIENT OXIDIZING-AGENT FOR DIHYDROXYBENZENES [J].

DURST, HD ;

MACK, MP ;

WUDL, F .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (02) :268-269

[8] Synthesis of the nonamannan residue of a glycoprotein with high mannose content [J].

Grice, P ;

Ley, SV ;

Pietruszka, J ;

Priepke, HWM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02) :197-200

[9] Preparation, structure, derivatisation and NMR data of cyclohexane-1,2-diacetal protected carbohydrates [J].

Grice, P ;

Ley, SV ;

Pietruszka, J ;

Priepke, HWM ;

Warriner, SL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04) :351-363

[10]

GRICE P, 1995, SYNLETT, P783

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