NAKED SUGARS AS SYNTHETIC INTERMEDIATES .26. SYNTHESIS OF ALPHA-D-(1-]3) AND ALPHA-D-(1-]4)-C-LINKED GALACTOSIDES OF D-MANNOSE DERIVATIVES - CONFORMATION OF ALPHA-C-GALACTOSIDES

被引：40

作者：

FERRITTO, R ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE, BCH DORIGNY, CHIM SECT, CH-1015 LAUSANNE, SWITZERLAND

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)86285-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reductive radical alpha-D-galactosidation of 5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7- -oxabicyclo[2.2.1]heptan-2-one with acetobromo-D-galactose, followed by ketone reduction led to (+)-(1R,2S, 3R,4S,5S,6S)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-[(2',3',4',6'-tetra-O-acetyl-alpha-D-galactopyranosyl)me- thyl]-7-oxabicyclo[2.2.1]heptan-2-endo-ol which was converted into (+)-methyl 3-deoxy-3-[(alpha-D-galactopyranosyl)methyl]-alpha-D-mannopyranoside (1), (+)-3-deoxy-3-[alpha-D-galactopyranosyl)methyl]-D-mannitol (2) and 4-deoxy-4-[(2',3',4',6'-tetra-O-acetyl-alpha-D-galactopyranosyl)methyl]-2,3,6-tri-O-acetyl-D-mannono-1,5-lactone (3). H-1-MNR data of the alpha-C-galactosides confirmed that their preferred conformations involve antiperiplanar arrangements for the C-linked substrates and bond sigma C(1'),C(2') of the alpha-(1-->3)-C-galactoside unit. The alpha-(1-->3)-C-galactoside of methyl mannopyranoside 1 adopts a conformation similar to that proposed for methyl 3-O-(alpha-D-galactopyranosyl)-alpha-D-mannopyranoside.

引用

页码：2077 / 2092

页数：16

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