6R-, and 6S, -6C-methylglucose from D-glucuronolactone: Efficient synthesis of a seven carbon fucose analogue: Inhibition of some enzymes of primary metabolism

✍ Scribed by Yves Blériot; Christian F. Masaguer; Joanne Charlwood; Bryan G Winchester; Alexandra L. Lane; Sarah Crook; David J. Watkin; George W.J. Fleet

• Book ID: 104208159
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 776 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10011-4

✦ Synopsis

Syntheses of the two epimeric 6C-methylglucoses from D-glucuronolactone rely on a nonstereoselective reduction of an intermediate lactol. A highly stereoselective reduction of a silylated lactol, which is accompanied by a silyl migration, gives easy access to 6S-6C-methylglucose -a seven carbon fucose analogue in five steps from glucuronolactone in an overall yield of 40%. An azido analogue of 6R-6C-methylglucose is also reported. Such compounds may provide new materials for the selective inhibition of various enzymes of primary metabolism including glucokinase, glucose-6-phosphatase, and phosphoglucomutase. X-ray crystal structures of (IS,3R,4S,5S, 7R~8R)-3-methy~-7~8-~-is~pr~py~idene-3~4~7~8-te~ahydr~xy-2~6-di~xabicyc~[3~3~]octane and 7-deoxy-1,2-5,6-di-O-isopropylidene-L-glycero-ot-D-gluco-heptofuranose are reported.