SYNTHESIS OF 2-DEOXY-L-HEPTOSE AND 2-DEOXY-D-GALACTO-HEPTOSE VIA INVERSE TYPE HETERO-DIELS-ALDER REACTION

被引：28

作者：

DEGAUDENZI, L ^{[1
]}

APPARAO, S ^{[1
]}

SCHMIDT, RR ^{[1
]}

机构：

[1] UNIV CONSTANCE,FAK CHEM,W-7750 CONSTANCE,GERMANY

来源：

TETRAHEDRON | 1990年 / 46卷 / 01期

关键词：

D O I：

10.1016/S0040-4020(01)97598-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Inverse type hetero-Diels-Alder reaction based diastereoselective synthesis of higher sugars is performed with chiral carbon substituents in the 2-position of the 1-oxa-13-diene required as heterodiene. This is demonstrated for the synthesis of partially protected 2-deoxy-L-galacto-heptose 16. Thus heterodienes 12ab obtained from L-ascorbic acid in high overall yield afforded with ethyl vinylether as heterodienophile preferentially the endo-adducts 13ab with the α-L-erythro isomers predominating. Structural proof came from transformation into the known 2-deoxy D-glucose derivative 21. © 1990.

引用

页码：277 / 290

页数：14

共 28 条

[1]

ALHKIM AH, 1985, SYNTHESIS-STUTTGART, P207

[2]

APPARAO S, 1987, SYNTHESIS-STUTTGART, P900

[3]

APPARAO S, 1987, SYNTHESIS-STUTTGART, P896

[4] A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF DL-OLEANDROSE [J].