引用本文:
Zhong Jun LI, He Qing HUANG, Meng Shen CAI. STEREOSELECTIVE AND MILD METHOD FOR THE SYNTHESIS OF α-D-MANNOPYRANOSIDES AND RELATED OLIGOSACCHARIDES IN HIGH YIELD[J]. Chinese Chemical Letters,
1994, 5(6): 477-480.
Citation: Zhong Jun LI, He Qing HUANG, Meng Shen CAI. STEREOSELECTIVE AND MILD METHOD FOR THE SYNTHESIS OF α-D-MANNOPYRANOSIDES AND RELATED OLIGOSACCHARIDES IN HIGH YIELD[J]. Chinese Chemical Letters, 1994, 5(6): 477-480.
Citation: Zhong Jun LI, He Qing HUANG, Meng Shen CAI. STEREOSELECTIVE AND MILD METHOD FOR THE SYNTHESIS OF α-D-MANNOPYRANOSIDES AND RELATED OLIGOSACCHARIDES IN HIGH YIELD[J]. Chinese Chemical Letters, 1994, 5(6): 477-480.
STEREOSELECTIVE AND MILD METHOD FOR THE SYNTHESIS OF α-D-MANNOPYRANOSIDES AND RELATED OLIGOSACCHARIDES IN HIGH YIELD
摘要:
Model reaction of 1-O-(3,5-dinitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-mannopyranose 1 with a series of carboxylic acids,phenols,alcohols and saccharides respectively demonstrated that stereocontrolled mannosyl transfer with the retention of configuration at the anomeric center was best carried out in dichloromethane (-20℃→r.t.) with TMSOTf as the Lewis acid catalyst,DBMP as a deprotic agent and powdered 3A molecular sieves as a desiccating agent.Under these conditions,α-D-mannopyranosides and related oligosaccharides were obtained in good yields.
English
STEREOSELECTIVE AND MILD METHOD FOR THE SYNTHESIS OF α-D-MANNOPYRANOSIDES AND RELATED OLIGOSACCHARIDES IN HIGH YIELD
Abstract:
Model reaction of 1-O-(3,5-dinitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-mannopyranose 1 with a series of carboxylic acids,phenols,alcohols and saccharides respectively demonstrated that stereocontrolled mannosyl transfer with the retention of configuration at the anomeric center was best carried out in dichloromethane (-20℃→r.t.) with TMSOTf as the Lewis acid catalyst,DBMP as a deprotic agent and powdered 3A molecular sieves as a desiccating agent.Under these conditions,α-D-mannopyranosides and related oligosaccharides were obtained in good yields.
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