Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4-deoxy-α- and β- l-lyxopyranosides

[Display omitted] Methyl 2,3-anhydro-4- O-methanesulfonyl-α- d-ribopyranoside ( 12) was prepared through a new six-step sequence starting from d-arabinose. Chemical behaviour of 12 was further studied under solvolytic conditions and in the presence of azide anion as a nucleophile. Factors governing...

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Published inCarbohydrate research Vol. 340; no. 11; pp. 1866 - 1871
Main Authors Popsavin, Velimir, Benedeković, Goran, Popsavin, Mirjana, Srećo, Bojana, Djoković, Dejan
Format Journal Article
LanguageEnglish
Published Netherlands Elsevier Ltd 15.08.2005
Subjects
2,3-Anhydro-lyxopyranosides
2,3-Anhydro-ribopyranosides
Arabinose - chemistry
Azides - chemistry
Azido sugars
Carbohydrate Conformation
Chromatography, Thin Layer
Epoxide ring opening
Epoxy Compounds - chemistry
Glycosides - chemistry
Magnetic Resonance Spectroscopy
Models, Chemical
Regioselectivity
Spectrophotometry, Infrared
Temperature
2,3-Anhydro-lyxopyranosides
Azido sugars
Epoxide ring opening
Regioselectivity
2,3-Anhydro-ribopyranosides
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Summary:[Display omitted] Methyl 2,3-anhydro-4- O-methanesulfonyl-α- d-ribopyranoside ( 12) was prepared through a new six-step sequence starting from d-arabinose. Chemical behaviour of 12 was further studied under solvolytic conditions and in the presence of azide anion as a nucleophile. Factors governing the regiochemistry of epoxide ring opening are briefly discussed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2005.06.006