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The reaction of 2,3-O-isopropyliden-4-iodo-4,6-didesoxy-α-methyl-L-talopyranoside and 2,3-O-isopropyliden-4-iodo-4,6-didesoxy-α-methyl-L-mannopyranoside with sodium azide was studied.
The substitution is completely or partially accompanied by rearrangement with ring contraction and formation of a furanoside structure. The possible mechanism of such transformations was examined.
The synthesis of 2,3-O-isopropyliden-5-acetamido-5,6-didesoxy-α-methyl-L-talofuranoside, 2,3-O-isopropyliden-5-acetamido-5,6-didesoxy-β-methyl-D-allofuranoside, and 2,3-O-isopropyliden-4-acetamido-4,6-didesoxy-α-methyl-L-talopyranoside was carried out.
KeywordsSodium Azide Monosaccharide Sodium Azide Ring Contraction
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