Photoreaction of methyl and phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-beta-D-erythro-hex-2-enopyranosides in methanol.
The title compounds were irradiated with a high-pressure mercury lamp in methanol to give 2-C-hydroxymethyl derivatives having the gluco, altro, and allo configurations as well as an S(N)2' product. Equatorial attack of a hydroxymethyl radical slightly predominated over axial attack. During chromatographic separation on a silica gel column, partial migration of the 4,6-O-benzylidene group in the gluco and altro products occurred to yield the 3',4-O-benzylidene derivatives.
Sakakibara
Tohru
T
Graduate School of Integrated Science, Yokohama City University, 22-2, Seto, Kanazawa-ku, Yokohama 236-0027, Japan. baratoru@yokohama-cu.ac.jp
Shindo
Tetsuya
T
Hirai
Hiroshi
H
D002236:Carbohydrate Conformation; D002845:Chromatography; D006027:Glycosides / Q000737:chemistry* / Q000528:radiation effects; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol; D010777:Photochemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry
D006027:Glycosides; D013450:Sulfones; D000432:Methanol