SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)

被引：0

作者：

FRICK, W ^{[1
]}

KRULLE, T ^{[1
]}

SCHMIDT, RR ^{[1
]}

机构：

[1] UNIV CONSTANCE,FAK CHEM,POSTFACH 5560,W-7750 CONSTANCE,GERMANY

来源：

LIEBIGS ANNALEN DER CHEMIE | 1991年 / 05期

关键词：

PHOSPHONIUM BROMIDE; (BENZYLOXY)(BENZYLOXYCARBONYL)METHYL]TRIPHENYL; WITTIG REACTION; D-MANNOSE ALDEHYDE; SYNTHESIS OF PER-0-PROTECTED; KDO, SYNTHESIS OF 4,5-7,8-DI-0-ISOPROPYLIDENE-PROTECTED;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[(Benzyloxy)(benzyloxycarbonyl)methyl]triphenylphosphonium bromide (8), obtained from glyoxylic acid via a convenient one-pot procedure, reacted in a Wittig reaction with 4-O-benzyl-2,3:5,6-di-O-isopropylidene-D-mannose (7), readily synthesized on a large scale from D-mannose, to provide the KDO derivative 9. Hydrogenolytic removal of the benzyl groups furnished directly the 4,5:7,8-di-O-isopropylidene protected KDO 11. Its treatment with diazomethane led to the known ester derivative 12-alpha, beta (2:1 anomeric mixture) which could be also obtained by transesterification of 9 and subsequent hydrogenolytic debenzylation.

引用

页码：435 / 438

页数：4

共 32 条

[1] SCOPE AND LIMITATIONS OF THE ALDOL CONDENSATION CATALYZED BY IMMOBILIZED ACYLNEURAMINATE PYRUVATE LYASE [J].

AUGE, C ;

BOUXOM, B ;

CAVAYE, B ;

GAUTHERON, C .

TETRAHEDRON LETTERS, 1989, 30 (17) :2217-2220

[2] 2,3,4,6-TETRA-OMICRON-BENZYL-D-GLUCOSYL CHLORIDE + ITS USE IN SYNTHESIS OF ALPHA- + BETA-ANOMERS OF 2-OMICRON-D-GLUCOSYLGLYCEROL + 4-OMICRON-D-GLUCOSYL-D-RIBITOL [J].

AUSTIN, PW ;

BUCHANAN, JG ;

HARDY, FE ;

BADDILEY, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :2128-&

[3] SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONATE-8-PHOSPHATE (KDO-8-P) FROM D-ARABINOSE - GENERATION OF D-ARABINOSE-5-PHOSPHATE USING HEXOKINASE [J].

BEDNARSKI, MD ;

CRANS, DC ;

DICOSIMO, R ;

SIMON, ES ;

STEIN, PD ;

WHITESIDES, GM .

TETRAHEDRON LETTERS, 1988, 29 (04) :427-430

[4]

BETZ R, 1984, ANGEW CHEM, V96, P420

[5]

BETZ R, 1984, ANGEW CHEM INT EDIT, V23, P430

[6] A NOVEL STRATEGY FOR THE SYNTHESIS OF AMMONIUM 3-DEOXY-D-MANNO-2-OCTULOSONATE (AMMONIUM KDO) FROM LOWER MONOSACCHARIDES - C-C BOND CONSTRUCTION AT C-6 OF D-MANNOSE VIA COBALOXIME-MEDIATED RADICAL ALKYL ALKENYL CROSS COUPLING [J].

BRANCHAUD, BP ;

MEIER, MS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1320-1326

[7] A SYNTHESIS OF AMMONIUM 3-DEOXY-D-MANNO-2-OCTULOSONATE (AMMONIUM KDO) FROM D-MANNOSE VIA COBALOXIME-MEDIATED RADICAL ALKYL-ALKENYL CROSS COUPLING [J].

BRANCHAUD, BP ;

MEIER, MS .

TETRAHEDRON LETTERS, 1988, 29 (26) :3191-3194

[8] CHEMICAL SYNTHESIS AND QUANTITATIVE ESTIMATION OF 3-DEOXY D-MANNO-OCTULOSONIC ACID [J].

CHARON, D ;

SARFATI, RS ;

STROBACH, DR ;

SZABO, L .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1969, 11 (02) :364-&

[9] SYNTHESIS OF 3-DEOXY-D-MANNO-OCTULOSONIC ACID (KDO) [J].

COLLINS, PM ;

OVEREND, WG ;

SHING, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (21) :1139-1140

[10] STEREOSELECTIVE TOTAL SYNTHESES OF THE NATURALLY-OCCURRING ENANTIOMERS OF N-ACETYLNEURAMINIC ACID AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID - A NEW AND STEREOSPECIFIC APPROACH TO SIALO AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONJUGATES [J].

DANISHEFSKY, SJ ;

DENINNO, MP ;

CHEN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :3929-3940

← 1 2 3 4 →