Chemical Synthesis of (4,6-Pyr)-Gal β1→4GlcNAcβ1→3Fucβ1→OMe: A Pyruvated Trisaccharide Related to the Cell Aggregation of the Sponge Microciona Prolifera

Shaojiang Deng State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

Biao Yu State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

Zhongwu Guo State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

Yongzheng Hui State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

Abstract

4,6-O-[(R)-1-carboxylethylidene]Galβ1 →4GlcNAcβ1 →3Fucβ1 →OMe, a pyruvated trisaccharide unit involved in the aggregation factor of the marine sponge Microciona prolifera, was synthesized stereospecifically and unambiguously employing thioglycosides as glycosyl donors to construct glycosidic bonds.

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Chemical Synthesis of (4,6-Pyr)-Gal β1→4GlcNAcβ1→3Fucβ1→OMe: A Pyruvated Trisaccharide Related to the Cell Aggregation of the Sponge Microciona Prolifera

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Chemical Synthesis of (4,6-Pyr)-Gal β1→4GlcNAcβ1→3Fucβ1→OMe: A Pyruvated Trisaccharide Related to the Cell Aggregation of the Sponge Microciona Prolifera

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