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Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars.

ABSTRACT: Alpha-mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thioglycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.

SUBMITTER: Crich D

PROVIDER: S-EPMC2852025 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars.

Crich David D Picard Sébastien S

The Journal of organic chemistry 20091201 24

Alpha-mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thioglycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed. ...[more]

PMID: 19924835

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