PubMed:15992785 / 377-460
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Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4-deoxy-alpha- and beta-L-lyxopyranosides.
Methyl 2,3-anhydro-4-O-methanesulfonyl-alpha-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.
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