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Thesis Name: Studies on stereoselective synthesis of phenylglycine using D-glucopyranosylimine as chiral template
Usage: Studies on stereoselective synthesis of phenylglycine using D-glucopyranosylimine as chiral template
Keyword: N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)aldimine; Chiral auxiliary; Phenylglycine
Remarks: The N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)aldimine was used as chiral template for stereoselective synthesis of phenylglycine. The phenylglycine can be synthesized stereoselectively by the tin tetrachloride lewis acid induced addition of trimethylsilyl cyanide to N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)aldimine in the dichloromethane with the addition of a small quantity of triethylamine and then by acid-catalyzed hydrolysis. The synthetic method is efficient, economical and friendly to environment, giving the high yield and high ratio of diastereomers.
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