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An improved synthesis of the 5-deoxy-5-(hydroxyphosphinyl)- d-glucopyranoses, and crystal structures of 1,2,3,4,6-penta-O-acetyl-5-deoxy-5-[(R)-methoxyphosphinyl]- β-d-glucopyranose and its 5-[(R)-ethylphosphinyl] congener

✍ Scribed by Thomas Richter; Peter Luger; Tadashi Hanaya; Hiroshi Yamamoto

Publisher
Elsevier Science
Year
1989
Tongue
English
Weight
772 KB
Volume
193
Category
Article
ISSN
0008-6215

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✦ Synopsis

Treatment of 3-0-acetyl-5-deoxy-5-(dimethoxyphosphinyl)-l,2-O-isopropylidene-cr-D-glucofuranose (7) with dihydropyran in the presence of pyridinium ptoluenesulfonate gave the 6-0-(tetrahydropyran-2-yl) derivative in 91% yield. Ring-enlargement of this compound by the known, 2-step procedure gave 5-deoxy-5-(hydroxyphosphinyl)-D-glucopyranoses in an overall yield from 7 twice as high as that obtained by the previous, alternative route via the corresponding 6-O-(triphenylmethyl)-cY-D-glucofuranose precursor. X-Ray crystallographic analyses were performed on the two title compounds, penta-0-acetyl-5-deoxy-5-(methoxyphosphinyl)-(l2b) and -5-(ethylphosphinyl)-p-D-glucopyranose (13b). The results show that both have the 4C, conformation and the substituents on C-l to C-5 are quasiequatorial (nomenclature of Jeffrey and Yates). The methoxy group of l2b is in a quasi-equatorial position, whereas the ethyl group of 13b is attached bisectionally to P-5.

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