Sugars Containing a Carbon-phosphorus Bond. VI. 5-(Alkylphosphinyl)-5-deoxy-D-xylopyranose

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概要

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• The reactions of diethyl ethylphosphonite with 3-<I>O</I>-acetyl-5-deoxy-5-iodo-1,2-<I>O</I>-isorpopylidine-α-D-xylofuranose (Ia) or 3-<I>O</I>-benzoyl-5-deoxy-5-iodo-1,2-<I>O</I>-isopropylidene-α-D-xylofuranose(Ib) afforded IIa or IIc, respectively. Similarly, using diethyl butylphosphonite in place of diethyl ethylphosphonite, IIb and IId were obtained. Treatment of IIb with methanolic sodium methoxide gave 5-deoxy-1,2-<I>O</I>-isopropylidene-5-(methoxybutylphosphinyl)-α-D-xylofuranose together with a small amount of 5-(3-<I>O</I>-cyclo-butylphosphinate)-5-deoxy-1,2-<I>O</I>-isopropylidene-α-D-xylofuranose(VII). Compound VII was also obtained from the reaction of 5-deoxy-5-iodo-1,2-<I>O</I>-isopropylidene-α-D-xylofuranose(VIII) and diethyl butylphosphonite. The reaction of IIa or IIc with sodium dihydrobis(2-methoxyethoxy)aluminate gave 5-deoxy-5-(ethylphosphinyl)-1,2-<I>O</I>-isopropylidene-α-D-xylofuranose(IIIa). Similarly, 5-(butylphosphinyl)-5-deoxy-1,2-<I>O</I>-isopropylidene-α-D-xylofuranose(IIIb) was obtained from IIb, IId, VI, and VII. Hydrolysis of IIIa and IIIb with sulfuric acid gave 5-deoxy-5-(ethyl-phosphinyl)-(IVa) and 5-(butylphosphinyl)-5-deoxy-D-xylopyranose(IVb), respectively. Acetylation of IVa and IVb with acetic anhydride in pyridine gave the corresponding <I>O</I>-acetates Va and Vb.

• 公益社団法人 日本化学会の論文

著者

• Inokawa Saburo

  Department of Chemistry Faculty of Science Kyoto University

• Seo Kuniaki

  Department of Industrial Chemistry, Numazu Technical College

• Seo Kuniaki

  Department of Applied Chemistry, College of Technology

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