Reductive ring opening of o-nitrobenzylidene acetals of monosaccharides: synthesis and photolysis of some photolabile sugars.
[figure: see text] A 6-O-o-nitrobenzyl methylglucoside and methylmannoside were synthesized by reacting 4,6-O-o-nitrobenzylidene acetals with triethylsilane and boron trifluoride etherate. A 2,6-di-O-o-nitrobenzyl and a 3,6-di-O-o-nitrobenzyl methylmannoside were obtained from a 2,3:4,6-di-O-o-nitrobenzylidene methylmannoside by the same method. The photolabile sugars obtained were deprotected by irradiation at 350 nm to afford methylglycosides.
Watanabe
S
S
Department of Biomolecular Science, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
Sueyoshi
T
T
Ichihara
M
M
Uehara
C
C
Iwamura
M
M
D001597:Benzylidene Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000528:radiation effects; D008958:Models, Molecular; D008968:Molecular Conformation; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000528:radiation effects; D010782:Photolysis; D013329:Structure-Activity Relationship
D001597:Benzylidene Compounds; D009005:Monosaccharides