Organic Letters
Organic Letters
4 years ago

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

Assistance of the C-7,8-Picoloyl Moiety for Directing the Glycosyl Acceptors into the α-Orientation for the Glycosylation of Sialyl Donors
Yow-Fu Tsai, Yu-Fa Wu
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 CH2Cl2. The methodology was successfully applied to the total synthesis of ganglioside Hp-s1 possessing neuritogenic activity.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01658

DOI: 10.1021/acs.orglett.7b01658

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