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2017•Organic LettersRequires access

Assistance of the C-7,8-Picoloyl Moiety for Directing the Glycosyl Acceptors into the α-Orientation for the Glycosylation of Sialyl Donors

Yu-Fa Wu, Yow‐Fu Tsai

Open publisher page 31 citations

Abstract

An efficient α-sialylation method for many primary hydroxyl acceptors that include 6-OH glycosides has been developed. 7,8-Di- O -picoloyl sialyl glycoside was used as the glycosyl donor, and α-glycoconjugation was controlled by using the 7,8-di- O -picoloyl moiety in CH 2 Cl 2 . The methodology was successfully applied to the total synthesis of ganglioside Hp-s1 possessing neuritogenic activity.

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What this paper is about

An efficient α-sialylation method for many primary hydroxyl acceptors that include 6-OH glycosides has been developed. 7,8-Di- O -picoloyl sialyl glycoside was used as the glycosyl donor, and α-glycoconjugation was controlled by using the 7,8-di- O -picoloyl moiety in CH 2 Cl 2 . The methodology was successfully applied to the total synthesis of ganglioside Hp-s1 possessing neuritogenic activity.

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Available abstract

An efficient α-sialylation method for many primary hydroxyl acceptors that include 6-OH glycosides has been developed. 7,8-Di- O -picoloyl sialyl glycoside was used as the glycosyl donor, and α-glycoconjugation was controlled by using the 7,8-di- O -picoloyl moiety in CH 2 Cl 2 . The methodology was successfully applied to the total synthesis of ganglioside Hp-s1 possessing neuritogenic activity.

Key concepts: Chemistry, Moiety, Glycosyl, Glycosylation, Glycosyl donor, Glycoside, Stereochemistry, Combinatorial chemistry

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Assistance of the C-7,8-Picoloyl Moiety for Directing the Glycosyl Acceptors into the α-Orientation for the Glycosylation of Sialyl Donors — Research Paper | ScholarLens