Stereoselective Dihydroxylation Reaction of Alkenyl ß-D-Hexopyranosides: A Methodology for the Synthesis of Glycosylglycerol Derivatives and 1-O-Acyl-3-O-ß-D-glycosyl-sn-glycerol Analogues

被引：7
|
作者：
Vega-Perez, Jose M. [1 ]
Palo-Nieto, Carlos [1 ]
Perinan, Ignacio [1 ]
Vega-Holm, Margarita [1 ]
Calderon-Montano, Jose M. [2 ]
Lopez-Lazaro, Miguel [2 ]
Iglesias-Guerra, Fernando [1 ]
机构：
[1] Univ Seville, Dept Quim Organ & Farmaceut, Fac Farm, Seville 41012, Spain
[2] Univ Seville, Dept Farmacol, Fac Farm, Seville, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 06期
关键词：
Synthetic methods; Asymmetric synthesis; Carbohydrates; Diastereo-selectivity; Biological activity; Dihydroxylation; POTENTIAL ANTICANCER DRUGS; TUMOR-PROMOTING ACTIVITY; ALLYLIC ALCOHOL SYSTEMS; ALKYLATING-AGENTS; ASYMMETRIC DIHYDROXYLATION; GLYCOGLYCEROLIPID ANALOGS; OSMIUM-TETROXIDE; NATURAL-PRODUCT; D-GLUCOSAMINE; D-GLUCO;
D O I：
10.1002/ejoc.201101539
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of new glycosylglycerol derivatives have been prepared by stereoselective dihydroxylation of a range of alkenyl beta-D-hexopyanosides under Donohoe's conditions. We have studied the relationship between the diastereoisomeric excess and the structural features of the precursor (sugar and alkenyl moieties). The stereochemical yields demonstrated that the presence of a hydrogen-bond donor group (OH, NHAc) at the 2-position of the sugar moiety is required to obtain high levels of stereofacial discrimination. New 1-O-acyl-3-O-beta-D-glycosyl-sn-glycerol analogues were obtained by functionalisation of the primary hydroxy group with a fatty acid. Preliminary cytotoxic activity assays of both glycosylglycerol and glycoglycerolipid analogues are also presented.
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收藏
页码：1237 / 1252
页数：16
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