Sugars Containing a Carbon-phosphorus Bond. VI. 5-(Alkylphosphinyl)-5-deoxy-D-xylopyranose
作者:Kuniaki Seo、Saburo Inokawa
DOI:10.1246/bcsj.48.1237
日期:1975.4
The reactions of diethyl ethylphosphonite with 3-O-acetyl-5-deoxy-5-iodo-1,2-O-isorpopylidine-α-d-xylofuranose (Ia) or 3-O-benzoyl-5-deoxy-5-iodo-1,2-O-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-O-isopropylidene-5-(methoxybutylphosphinyl)-α-d-xylofuranose together with a small amount of 5-(3-O-cyclo-butylphosphinate)-5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose(VII). Compound VII was also obtained from the reaction of 5-deoxy-5-iodo-1,2-O-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-O-isopropylidene-α-d-xylofuranose(IIIa). Similarly, 5-(butylphosphinyl)-5-deoxy-1,2-O-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 O-acetates Va and Vb.
IVb)。