STEREOSELECTIVE SYNTHESIS OF METHYL BETA-DL-NOVIOSIDE

被引：48

作者：

ACHMATOWICZ, O ^{[1
]}

GRYNKIEWICZ, G ^{[1
]}

SZECHNER, B ^{[1
]}

机构：

[1] POLISH ACAD SCI, INST ORG CHEM, PL-00961 WARSAW, POLAND

来源：

TETRAHEDRON | 1976年 / 32卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)83234-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective synthesis of an antibiotic sugar, methyl .beta.-DL-novioside from 2-(2-furyl)propan-2-ol is described. The key step involved transformation of 2,5-dimethoxy-2,5-dihydrofuran derivative into 2,3-unsaturated pyranos-4-ulose. Its glycosidation followed by reduction, methylation and hydroxylation afforded .beta.-DL-novioside. The anomeric configuration of methyl noviosides and novobiocin are oppisite to that reported in the literature.

引用

页码：1051 / 1054

页数：4

共 23 条

[1] ACHMATOWICZ O, 1973, ROCZ CHEM, V47, P1223
[2] ACHMATOWICZ O, 1972, ROCZ CHEM, V46, P2241
[3] ACHMATOWICZ O, 1973, B ACAD POL SCI-CHIM, V21, P181
[4] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES
ACHMATOWICZ, O
BUKOWSKI, P
SZECHNER, B
ZWIERZCHOWSKA, Z
ZAMOJSKI, A
[J]. TETRAHEDRON, 1971, 27 (10) : 1973 - +
[5] [Anonymous], CARBOHYD RES
[6] BREITMAIER E, 1974, 13C NMR SPECTROSCOPY, P226
[7] DUNLOP AP, 1953, FURANS, P258
[8] DURETTE PL, 1971, ADV CARBOHYD CHEM BI, V26, P122
[9] FERRIER RJ, 1969, ADV CARBOHYD CHEM BI, V24, P265
[10] CONFORMATIONS .6. VINYL-ALLYLIC PROTON SPIN COUPLINGS
GARBISCH, EW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) : 5561 - +

← 1 2 3 →