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

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 4 R ( 2a– e) and 4 S ( 3a– e) configurations. The presence...

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Bibliographic Details
Published in:Carbohydrate research 2005-12, Vol.340 (17), p.2583-2589
Main Authors: Çetin, Fatma, Yenil, Nilgün, Yüceer, Levent
Format: Article
Language:English
Subjects:
Antibiotics
Antimalarial drugs
Deoxy Sugars - chemical synthesis
Deoxy Sugars - chemistry
Deoxy Sugars - radiation effects
Endoperoxides
Furano sugars
Magnetic Resonance Spectroscopy
Models, Molecular
Oxidation-Reduction
Peroxides - chemical synthesis
Peroxides - chemistry
Peroxides - radiation effects
Photochemistry
Spectrometry, Mass, Electrospray Ionization
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Spiro Compounds - radiation effects
Spiroketals
Sunlight
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Summary: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 4 R ( 2a– e) and 4 S ( 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 4 S isomers. 3- O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3- O-methyl derivatives gave pure single stereoisomers.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2005.09.006