Abstract
This paper deals with the partial correction of our previous paper1) and with some new results in regard to ammonolysis of the epoxide ring of 2, 3-anhydroribofuranoside derivatives. Treatment of methyl 2, 3-anhydro-5-deoxy-α-D-ribofuranoside, prepared from D-xylose, with ammonia gave methyl 2-amino-2, 5-dideoxy-α-D-arabinoside and no methyl 3-amino-3, 5-dideoxy-α-D-xyloside which we reported to obtain previously. The exclusive attack of the nucleophilic reagent at C-2 is inconsistent with a result of C. D. Anderson et al.6) in regard to ammonolysis of methyl 2, 3-anhydro-α-D-ribofuranoside. In contrast to α-anomer, methyl 2, 3-anhydro-5-deoxy-β-D-ribofuranoside gave mainly methyl 3-amino-3, 5-dideoxy-β-D-xyloside. The difference of ammonolysis products between α- and β-anomer will be due to existence of steric hindrance.
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