A new route to D-xylo-hexos-5-ulose and some of its selectively protected derivatives from D-galactose

被引：18

作者：

Barili, PL ^{[1
]}

Berti, G ^{[1
]}

Catelani, G ^{[1
]}

DAndrea, F ^{[1
]}

DeRensis, F ^{[1
]}

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,I-56126 PISA,ITALY

来源：

TETRAHEDRON | 1997年 / 53卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(97)00536-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to D-xylo-hexos-5-ulose, a useful synthetic intermediate, is described, starting from methyl beta-D-galactopyranoside and involving as the key step an epoxidation/methanolysis of 3-O-protected methyl 2,6-di-O-benzyl-4-deoxy-alpha-L-threo-hex-4-enopyranosides, to produce bis-glycosides of the parent dicarbonylic sugar, which can be obtained free or selectively protected through hydrogenolytic and/or hydrolytic procedures. The diastereo- and regioselectivity of the epoxidation and solvolysis steps are investigated and tentatively interpreted, and new products characterized by NMR techniques, (C) 1997 Elsevier Science Ltd.

引用

页码：8665 / 8674

页数：10

共 13 条

[1] A FACILE CONVERSION OF 3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDES INTO 4-DEOXY-ALPHA-L-THREO-HEX-4-ENOPYRANOSIDE AND L-ARABINO-HEXOS-5-ULOSE DERIVATIVES [J].

BARILI, PL ;

BERTI, G ;

CATELANI, G ;

COLONNA, F ;

DANDREA, F .

CARBOHYDRATE RESEARCH, 1989, 190 (01) :13-21

[2] A SIMPLE STEREOSPECIFIC ROUTE TO 5-C-ALKOXY-D-GALACTOPYRANOSIDES AND TO L-ARABINO-HEXOS-5-ULOSES [J].

BARILI, PL ;

BERTI, G ;

CATELANI, G ;

DANDREA, F .

TETRAHEDRON LETTERS, 1991, 32 (07) :959-962

[3] Double reductive amination of L-arabino-hexos-5-uloses: A diastereoselective approach to 1-deoxy-D-galactostatin derivatives [J].

Barili, PL ;

Berti, G ;

Catelani, G ;

DAndrea, F ;

DeRensis, F ;

Puccioni, L .

TETRAHEDRON, 1997, 53 (09) :3407-3416

[4]

BARILI PL, 1992, GAZZ CHIM ITAL, V122, P135

[5] EXPEDITIOUS SYNTHESIS OF AZASUGARS BY THE DOUBLE REDUCTIVE AMINATION OF DICARBONYL SUGARS [J].

BAXTER, EW ;

REITZ, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3175-3185

[6] CONCISE SYNTHESIS OF 1-DEOXYMANNOJIRIMYCIN [J].

BAXTER, EW ;

REITZ, AB .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (11) :1419-1422

[7] A SIMPLE AND HIGHLY DIASTEREOSELECTIVE PREPARATION OF GLYCAL EPOXIDES USING THE MCPBA-KF COMPLEX [J].

BELLUCCI, G ;

CATELANI, G ;

CHIAPPE, C ;

DANDREA, F .

TETRAHEDRON LETTERS, 1994, 35 (45) :8433-8436

[8]

Berti G., 1973, Topics in Stereochemistry, V7, P93

[9]

BUCHANAN JG, 1972, SELECTIVE ORGANIC TR, V1, P1

[10]

HELFERICH B, 1931, Z PHYSL CHEM, V200, P263

← 1 2 →