In:
Chinese Journal of Chemistry, Wiley, Vol. 40, No. 15 ( 2022-08), p. 1799-1806
Abstract:
An efficient synthesis of a complex tetrasaccharide fragment 1 structurally related to rhamnogalacturonan II side chain A has been accomplished through a stepwise glycosylation strategy. Challenges involved in the synthesis include the facile construction of the sterically crowded l ‐fucopyranose core and the stereoselective formation of two 1,2‐ cis ‐glycosidic linkages. The 3,4‐disubstituted l ‐fucopyranoside structure was successfully constructed through a ‘counterclockwise’ glycosylation sequence, namely, the less reactive axial 4‐OH group of the central fucose unit was glycosylated first, then the 3‐OH. Besides, a 2‐pyridinecarbonyl‐assisted α‐ d ‐xylosylation was developed to synthesize the α‐ d ‐xylopyranosidic linkage and a 3,4‐ O ‐benzoyl‐controlled α‐ l ‐galactosylation reaction was used for the stereoselective synthesis of the corresponding α‐ l ‐galactopyranosidic linkage.
Type of Medium:
Online Resource
ISSN:
1001-604X
,
1614-7065
DOI:
10.1002/cjoc.202200177
Language:
English
Publisher:
Wiley
Publication Date:
2022
detail.hit.zdb_id:
2144352-X
SSG:
6,25