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

V Popsavin, G Benedeković, M Popsavin, B Srećo…

Index: Popsavin, Velimir; Benedekovic, Goran; Popsavin, Mirjana; Sreco, Bojana; Djokovic, Dejan Carbohydrate Research, 2005 , vol. 340, # 11 p. 1866 - 1871

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Citation Number: 2

Abstract

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.