Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-D-xylo-oct-1,4-furano-7-uloses
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Date
2005
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Abstract
Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-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. © 2005 Elsevier Ltd. All rights reserved.
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Deoxy Sugars , Magnetic Resonance Spectroscopy , Models, Molecular , Oxidation-Reduction , Peroxides , Photochemistry , Spectrometry, Mass, Electrospray Ionization , Spiro Compounds , Sunlight , Antibiotics , Derivatives , Isomers , 3 o acetyl 5 eno 1,2 o isopropylidene 5,6,8 trideoxy alpha xylo 1,4 furano 7 ulose , 5 eno 3 o methyl 1,2 o trichloroethylidene 5,6,8 trideoxy alpha xylo 1,4 furano 7 ulose , carbohydrate derivative , carbon tetrachloride , endoperoxide , unclassified drug , article , photooxidation , priority journal , stereoisomerism , sunlight , Endoperoxides , Furano sugars , Carbohydrates