STEREOSELECTIVE REDUCTION OF 3-O-HEXOFURANOSYL S-METHYL DITHIOCARBONATES WITH TRIBUTYLTIN DEUTERIDE

被引：18

作者：

PATRONI, JJ ^{[1
]}

STICK, RV ^{[1
]}

机构：

[1] UNIV WESTERN AUSTRALIA,DEPT ORGAN CHEM,NEDLANDS 6009,W AUSTRALIA,AUSTRALIA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1979年 / 32卷 / 02期

关键词：

D O I：

10.1071/CH9790411

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reduction of several 3-O-hexofuranosyl (gluco, allo, galacto, gulo) S-methyl dithiocarbonates with tributyltin deuteride leads to highly stereoselective syntheses of 3-deoxy-[3-2H]hexofuranoses. Correspondingly, the reduction of the 3-O-[3-2H]hexofuranosyl (allo, gulo) S-methyl dithiocarbonates with tributyltin hydride leads to the epimeric (C 3) 3-deoxy-[3-2H]hexofuranoses, and the reduction with tributyltin deuteride leads to the 3-deoxy-[3, 3-2H2]hexofuranoses. © 1979, CSIRO. All rights reserved.

引用

页码：411 / 416

页数：6

共 12 条

[1] Baker, 1976, METHODS CARBOHYDR CH, V7, P3
[2] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS
BARTON, DHR
MCCOMBIE, SW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16): : 1574 - 1585
[3] NUCLEOPHILIC DISPLACEMENT REACTIONS IN CARBOHYDRATES .3. DISPLACEMENTS WITH 1,2-5,6-DI-O-ISOPROPYLIDENE-3-O-TOLUENE-P-SULPHONYL-ALPHA-D-GULOFURANOSE
BRIMACOM.JS
GENT, PA
STACEY, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (05): : 567 - &
[4] SYNTHESIS OF ABEQUOSE (3,6-DIDEOXY-D-XYLO-HEXOSE)
COPELAND, C
STICK, RV
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (06) : 1269 - 1273
[5] CONFORMATIONAL STUDIES ON 1,2-5,6-DI-O-ISOPROPYLIDENE-D-HEXOSES
HALL, LD
TRACEY, AS
SLESSOR, KN
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (12): : 1912 - &
[6] CHLORODEOXY AND DEOXY SUGARS
HAYLOCK, CR
MELTON, LD
SLESSOR, KN
TRACEY, AS
[J]. CARBOHYDRATE RESEARCH, 1971, 16 (02) : 375 - &
[7] KOCH JH, 1970, CARBOHYD RES, V15, P403
[8] STEREOSELECTIVE REDUCTION OF 3-O-HEXOFURANOSYL S-METHYL DITHIOCARBONATES WITH TRIBUTYLTIN DEUTERIDE
PATRONI, JJ
STICK, RV
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (11) : 449 - 450
[9] 1,2,5,6-DI-O-ISOPROPYLIDENE-D-HEXOFURANOSES ANX THEIR 3-KETO DERIVATIVES
SLESSOR, KN
TRACEY, AS
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (21): : 3989 - &
[10] UNSATURATED DERIVATIVES OF 1,2,5,6-DI-O-ISOPROPYLIDENE-D-HEXOFURAN-3-ULOSES
SLESSOR, KN
TRACEY, AS
[J]. CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1970, 48 (18): : 2900 - +

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