Syntheses of Carbocyclic Analogues of α-D-Glucosamine, α-D-Mannose, α-D-Mannuronic Acid, β-L-Idosamine, and β-L-Gulose

被引：11
|
作者：
Sun, Yunshan [1 ]
Nitz, Mark [1 ]
机构：
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 17期
基金：
加拿大健康研究院;
关键词：
PSEUDO-SUGARS; D-MANNOPYRANOSE; ENANTIOSELECTIVE SYNTHESIS; BUILDING-BLOCKS; RING-CLOSURE; DERIVATIVES; ACCESS; CYCLOHEXANONES; PENTAACETATES; REARRANGEMENT;
D O I：
10.1021/jo301240j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A versatile synthesis of orthogonally protected derivatives of carba-alpha-D-glucosamine, carba-alpha-D-mannose, carba-alpha-D-mannuronic acid, carba-beta-L-idosamine, and carba-beta-L-gulose from methyl alpha-D-mannoside is described. Our synthetic strategy utilizes the palladium-promoted Ferrier carbocyclization and persistent butane-2,3-diacetal protection to produce a key chiral cyclohexanone intermediate, from which all five carbasugar derivatives can readily be obtained.
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页码：7401 / 7410
页数：10
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