Synthesis of L-Iduronic Acid Derivatives: Crystal Structure of Methyl (Methyl 2,3,4-Tri-O-Acetyl-β-L-Idopyranosid)Uronate
作者:
Dennis M. Whitfield,
George I. Birnbaum,
Henrianna Pang,
Jose Baptista,
Bibudhendra Sarkar,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1991)
卷期:
Volume 10,
issue 3
页码: 329-348
ISSN:0732-8303
年代: 1991
DOI:10.1080/07328309108543912
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Several L-iduronic acid derivatives were prepared by chemical synthesis including the reducing sugar, the α– and ß-methyl glycosides and L-iduronolactone. The ß-methyl glycoside, as well as two isomeric orthoesters, were the unexpected products of glycosylation of methyl (2,3,4-tri-O-acetyl-α-L-idopyranosyl bromide) uronate. EI-MS was used to distinguish between the orthoesters and the glycosides. The crystal structure of the ß-methyl glycoside was determined by direct methods and refined by full-matrix least squares to a final value of R = 0.067 for 1739 reflections. The pyran ring was found to occur in the1C4 conformation, with the three acetoxy substituents in axial orientations. In aqueous solution, the α-anomer of the reducing sodium salt is almost entirely in a2SO ring conformation and the α-methyl glycoside is an equilibrium mixture of conformations which is sensitive to pH: The ß-anomers all have spectral data consistent with predominant or only slightly distorted1C4 chairs.
点击下载:
PDF (790KB)
返 回