D-グルコース誘導体(3-置換メチレン-3-デオキシ糖)のイオン交換樹脂による環化反応

概要

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3-(E)-and-(Z)-Cyanomethylene-(5a), (5b), p-nitrophenylmethylene (6a), (6b), p-methoxyphenylmethylene (7a), (7b) and phenylmethylene (8a), (8b)-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-ribo-hexofuranose were prepared from 1,2;5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (4) and the corresponding Wittig reagents. In deacetonylations of these 3-methylene derivatives by ion exchange resin (IR-120B), 5a, 5b and 6a, 6b gave rise to intramolecular cyclization products, 3,6-anhydro-3α-cyanomethyl-1,2-O-isopropylidene-α-D-glucofuranose (9) and 3,6-anhydro-3α-p-nitrophenylmethyl-1,2-O-isopropylidene-α-D-glucofuranose (11), respectively. While, 7a, 7b and 8a, 8b gave rise to the corresponding diol : 3-(E)-and-(Z)-p-methoxyphenylmethylene-3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose (12a), (12b) and 3-(E)- and-(Z)-phenylmethylene-3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose (13a), (13b).
社団法人日本薬学会の論文
1988-01-25