Synthesis of trehazolin beta-anomer.
Synthesis of trehazolin beta-anomer (3) from a D-glucose derived azido alcohol (4), was accomplished. 2-Chloro-1-methylpyridinium iodide was used in place of 2-chloro-3-ethylbenzoxazolium tetrafluoroborate as a means of preventing concomitant anomerization. Evaluation of compound (3) reveals that the stereochemistry of the anomeric position is significant for generation of inhibitory activities towards trehalases.
Kobayashi
Y
Y
Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Shiozaki
M
M
D000818:Animals; D012831:Bombyx; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000494:pharmacology*; D008969:Molecular Sequence Data; D013237:Stereoisomerism; D013552:Swine; D014198:Trehalase / Q000037:antagonists & inhibitors*
D004187:Disaccharides; C071816:trehazolin; D014198:Trehalase