NEW SYNTHESIS OF 4-DEOXY-D-GLUCOSE

被引：3

作者：

BROCKHAUS, M ^{[1
]}

FUCHS, EF ^{[1
]}

LEHMANN, J ^{[1
]}

机构：

[1] UNIV FREIBURG,CHEM LAB,D-7800 FREIBURG,FED REP GER

来源：

CHEMISCHE BERICHTE-RECUEIL | 1978年 / 111卷 / 02期

关键词：

D O I：

10.1002/cber.19781110243

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A New Synthesis of 4‐Deoxy‐D‐glucose A modified and improved method for the synthesis of 4‐deoxy‐D‐glucose (4) is described. The key product is methyl 2,3,6‐tri‐O‐acetyl‐4‐benzoylthio‐4‐deoxy‐α‐D‐galactopyranoside (3) which readily undergoes reductive desulfurization with Raney nickel. Subsequent deacetylation and hydrolysis yield 4‐deoxy‐D‐glucose (4). Copyright © 1978 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

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页码：811 / 813

页数：3

相关论文

共 11 条

[1]

BEMEK J, 1973, EUR J BIOCHEM, V40, P195

[2] CARBOHYDRATE SUBSTRATES FOR SKIN CELLS [J].

CARNEY, SA ;

LAWRENCE, JC ;

RICKETTS, CR .

BIOCHEMICAL JOURNAL, 1962, 83 (03) :533-+

[3] DESOXYZUCKER .3. UBER REAKTIONEN DER 2-O-TOSYL-1,6-3,4-DIANHYDRO-BETA-D-GALAKTO-PYRANOSE DARSTELLUNG VON 4-DESOXY-D-XYLOHEXOSE (4-DESOXY-D-GLUCOSE) UND 4-DESOXY-D-ARABINOHEXOSE (4-DESOXY-D-ALTROSE) [J].

CERNY, M ;

PACAK, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1962, 27 (01) :94-&

[4] METHYL 3,4-ANHYDRO-BETA-D-GALACTOPYRANOSIDE .1. REDUCTION [J].

DAHLGARD, M ;

CHASTAIN, BH ;

HAN, RJL .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :929-+

[5] IMPROVED METHOD FOR SPECIFIC RELEASE OR ACYLATION OF PRIMARY HYDROXYL-GROUPS FROM PERTRIMETHYLSILYLATED POLYOLS [J].

FUCHS, EF ;

LEHMANN, J .

CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (02) :721-724

[6] STRUCTURE AND REACTIVITY OF ANHYDRO-SUGARS .5. 3-DEOXY-D-RIBO-HEXOPYRANOSE AND 4-DEOXY D-XYLO-HEXOPYRANOSE [J].

HEDGLEY, EJ ;

RENNIE, RAC ;

OVEREND, WG .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (OCT) :4701-&

[7]

KOCHETKOV NK, 1970, IAN SSSR KH, P404

[8] Optical superposition and the 4 6-benzylidenemethylglucosides [J].

Mathers, DS ;

Robertson, GJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1933, :696-698

[9] SELECTIVE BLOCKING OF SACCHARIDES BY TRANSACETALIZATION WITH CYCLOHEXANONE ETHYLENE ACETAL - SYNTHESIS OF 4-DEOXY-D-XYLO-HEXOPYRANOSE [J].

PAULSEN, H ;

SALZBURG, H ;

REDLICH, H .

CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (11) :3598-3605

[10]

SIEWERT G, 1968, LIEBIGS ANN CHEM, V720, P161