Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-alpha-D-xylo-oct-1,4-furano-7-uloses.
Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers.
Cetin
Fatma
F
Ege University, Faculty of Science, Chemistry Department, Bornova, Izmir 35100, Turkey.
Yenil
Nilgün
N
Yüceer
Levent
L
D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D010777:Photochemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D013472:Sunlight
D003837:Deoxy Sugars; D010545:Peroxides; D013141:Spiro Compounds