Synthesis of erythro and threo furanoid glycals from 1-and 2-phenylselenenyl-carbohydrate derivatives

被引：21

作者：

Bravo, F ^{[1
]}

Kassou, M ^{[1
]}

Díaz, Y ^{[1
]}

Castillón, S ^{[1
]}

机构：

[1] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, E-43005 Tarragona, Spain

来源：

CARBOHYDRATE RESEARCH | 2001年 / 336卷 / 02期

关键词：

glycal synthesis; selenoglycosides; 1,4-anhydro-2-phenylselenenyl-pentitols; selenoxide elimination; double bond formation;

D O I：

10.1016/S0008-6215(01)00256-7

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：

Differently protected erythro and threo furanoid glycals were synthesized by selenoxide elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions ((BuOOH)-Bu-i, Ti((OPr)-Pr-i)(4), (Et2PrN)-Pr-i). The phenyl 1-selenoglycosides were obtained from methyl 2-deoxy-D-erythro-pentofuranoside by protection of the primary hydroxyl or both hydroxyls and further reaction with PhSeH in the presence of BF3. Et2O. Erythro and threo furanoid glycals were also prepared by treating 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols under similar conditions. The 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols were obtained from 4-pentene-1,2,3-triols by a 5-endo selenium electrophilic induced cyclization. (C) 2001 Published by Elsevier Science Ltd.

引用

页码：83 / 97

页数：15

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