Action of Grignard reagents on hexuronic esters and attempted dehydration of tertiary alcohols to give hex-5-enopyranosides
作者:
Gerald O. Aspinall,
Osamu Igarashi,
Thinnayam N. Krishnamurthy,
Walter Mitura,
Masuo Funabashi,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1976)
卷期:
Volume 54,
issue 11
页码: 1708-1713
ISSN:0008-4042
年代: 1976
DOI:10.1139/v76-243
出版商: NRC Research Press
数据来源: NRC
摘要:
The attempted formation of hex-5-enopyranosides from glycosiduronates by the action of Grignard reagents followed by dehydration affords hex-6-enopyranosides or 1,6-anhydrohexopyranoses as major products.13C nmr spectra of 6,6-di-C-substituted hexose derivatives are compared with those of a number of structurally related compounds. The formation of a hex-5-enopyranoside and the selective cleavage of its glycosidic linkage is illustrated by the synthesis and controlled hydrolysis of methyl 6-O-(6-deoxy-2,3,4-tri-O-methyl-β-L-arabino-hex-5-enopyranosyl)-2,3,4-tri-O-methyl-β-D-glucopyranoside(2).
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