NUCLEOPHILIC DISPLACEMENT REACTIONS IN CARBOHYDRATES .9. SOLVOLYSIS OF METHYL 6-0-METHANESULPHONYL-2,3-DI-0-METHYL-BETA-D-GALACTOPYRANOSIDE - A METHOXY-GROUP PARTICIPATION

被引：8

作者：

BRIMACOM.JS

CHING, OA

机构：

[1] Chemistry Department, The University

来源：

CARBOHYDRATE RESEARCH | 1969年 / 9卷 / 03期

关键词：

D O I：

10.1016/S0008-6215(00)80166-4

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The solvolysis of methyl 6-O-methanesulphonyl-2,3-di-O-methyl-β-d-galactoyranoside (8) in boiling 50% aqueous methanol, in the presence of sodium acetate afforded three products which were identified as methyl 3,6-anhydro-2-O-methyl-β-d-galactopyranoside (9), methyl 2,3,6-tri-O-methyl-β-d-galactopyranoside (12), and methyl 2,3-di-O-methyl-β-d-galactopyranoside (7). Anhydro-sugar 9 is considered to result from attack of solvent on an oxonium-ion intermediate 14, formed as a consequence of methoxy-group participation in displacement of the sulphonic ester group, while compounds 7 and 12 may result either from solvent attack upon the oxonium ion or from a solvent-assisted displacement of the sulphonic ester group. © 1969.

引用

页码：287 / &

共 27 条

[1] ROLE OF NEIGHBORING GROUPS IN REPLACEMENT REACTIONS .29. 5-METHOXYL PARTICIPATION AND LITHIUM ALUMINUM HYDRIDE REDUCTION
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[2] 6-METHOXYL PARTICIPATION AND ION PAIRS IN SOME SOLVOLYSIS REACTIONS
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[3] ROLE OF NEIGHBORING GROUPS IN REPLACEMENT REACTIONS .27. 5-METHOXYL PARTICIPATION IN SOME SOLVOLYSIS REACTIONS
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[4] 5-METHOXYL PARTICIPATION IN ACETOLYSIS . ION AND ION-PAIR INTERMEDIATES
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[5] DEALKYLATION AND DEACYLATION OF CARBOHYDRATE DERIVATIVES WITH BORON TRICHLORIDE AND BORON TRIBROMIDE
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[6] NUCLEOPHILIC DISPLACEMENT REACTIONS IN CARBOHYDRATES .6. SOLVOLYSIS OF METHYL 2,3-DI-O-BENZYL-6-O-METHYLSULPHONYL-BETA-D-GALCTOPYRANOSIDE - PARTICIPATION BY A BENZYLOXY-GROUP
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[7] BRIMACOMBE JS, 1968, CARBOHYD RES, V8, P376
[8] BRIMACOMBE JS, UNPUBLISHED RESULTS
[9] BRIMACOMBE JS, 1966, CARBOHYD RES, V2, P167
[10] BRIMACOMBE JS, 1967, CARBOHYD RES, V5, P239

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