Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
On the Possibility of Direct O-1β→ -6 Acyl Migration in 1-O-Acyl-β-D-glucose Derivatives
吉本 公浩津田 喜典
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キーワード: tuliposide
ジャーナル フリー

1983 年 31 巻 12 号 p. 4335-4340

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抄録
In order to clarify whether or not direct O-1β→ -6 acyl migration in O-acyl-D-glucose derivatives really occurs, 3-O-methyl-1-O-myristoyl-β-D-glucopyranose and 3-deoxy-1-O-myristoyl-β-D-glucopyranose were synthesized and their acyl migration was examined under thermal, solvolytic, and base- and acid-catalyzed conditions. Neither compound showed any tendency for acyl migration under these conditions (only partial solvolysis was observed under solvolytic conditions). Consequently, it was concluded that O-1β→ -6 acyl migration does not occur directly, but proceeds through the path O-1β→ -3→ -6.
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© The Pharmaceutical Society of Japan
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