Organocatalytic Synthesis of Higher-Carbon Sugars: Efficient Protocol for the Synthesis of Natural Sedoheptulose and D-Glycero-L-galacto-oct-2-ulose

被引：3

作者：

Popik, Oskar ^{[1
]}

Pasternak-Suder, Monika ^{[2
]}

Bas, Sebastian ^{[2
]}

Mlynarski, Jacek ^{[1
,2
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Jagiellonian Univ, Fac Chem, PL-30060 Krakow, Poland

来源：

CHEMISTRYOPEN | 2015年 / 4卷 / 06期

关键词：

aldol reaction; asymmetric synthesis; carbohydrates; natural products; organocatalysis; L-GALACTO-OCTULOSE; DE-NOVO SYNTHESIS; ALDOL REACTIONS; UNSATURATED PRECURSORS; HIGHER MONOSACCHARIDES; DIHYDROXYACETONE; DERIVATIVES; ACID; OSMYLATION; CHEMISTRY;

D O I：

10.1002/open.201500099

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we report a short and efficient protocol for the synthesis of naturally occurring higher-carbon sugars-sedoheptulose (D-altro-hept-2-ulose) and D-glycero-L-galacto-oct-2-ulosefrom readily available sugar aldehydes and dihydroxyacetone (DHA). The key step includes a diastereoselective organocatalytic syn-selective aldol reaction of DHA with D-erythrose and D-xylose, respectively. The methodology presented can be expanded to the synthesis of various higher sugars by means of syn-selective carbon-carbon-bond-forming aldol reactions promoted by primary-based organocatalysts. For example, this methodology provided useful access to D-glycero-D-galactooct-2-ulose and 1-deoxy-D-glycero-D-galacto-oct-2-ulose from D-arabinose in high yield (85 and 74%, respectively) and high stereoselectivity (99: 1).

引用

页码：717 / 721

页数：5

共 30 条

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