Preparation of various C-2 branched carbohydrates using intramolecular radical reactions.
A new and efficient method for the facile synthesis of C-2 branched carbohydrates has been developed using an intramolecular radical cyclization fragmentation reaction. The desired C-2 branched glucopyranosides were isolated in 40-84% yield. Additionally, an unexpected furanoside was obtained from a tributyltin iodide-promoted rearrangement of the radical intermediate. The C-2 formyl glycal was also isolated in good yield using tris(trimethylsilyl)silane (TTMSS) as the reducing agent. This method was extended to synthesize a beta C-2 branched glucopyranoside, a C-2 branched galactoside and a C-2 cyano glucopyranoside.
Choe
S W
SW
Department of Chemistry and Biochemistry, Loyola Marymount University, Los Angeles, CA 90045-8225, USA. tchoe@lmumail.lmu.edu
Jung
M E
ME
D002236:Carbohydrate Conformation; D003486:Cyanides / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000737:chemistry; D005697:Galactosides / Q000737:chemistry; D005936:Glucans / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D003486:Cyanides; D005663:Furans; D005697:Galactosides; D005936:Glucans