Abstract
Treatment of 3-O-acetyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D- xylofuranose (1c) with sodium dihydrobis(methoxyethoxy)aluminate, followed by the action of mineral acid and hydrogen peroxide, gave 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylopyranose (4a). The 3-O-benzyl derivative 4c was similarly obtained from the corresponding 3-O-benzyl-α-D-xylofuranose 1b. Diazotization of 3-O-acetyl-6-amino-5,6-dideoxy-5-C-(dimethoxyphosphinyl)-1,2-O-isopropylidene- α-D-glucofuranose (12), followed by hydrolysis and then treatment with chlorotriphenylmethane in pyridine, afforded the corresponding 5-deoxy-6-O-triphenylmethyl derivative 17. Similar ring enlargement of 17 exclusively yielded 5-deoxy-5-C-(hydroxyphosphinyl)-D-glucopyranose. The structures of these phosphorus sugar analogues were established on the basis of mass and 400-MHz 1H NMR spectra of the per-O-acetyl-5-deoxy-5-C-(methoxyphosphinyl) derivatives 6-9 and 21-25.
| Original language | English |
|---|---|
| Pages (from-to) | 3516-3521 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 50 |
| Issue number | 19 |
| Publication status | Published - 1985 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranoses. / Yamamoto, Hiroshi; Hanaya, Tadashi; Kawamoto, Heizan; Inokawa, Saburo; Yamashita, Mitsuji; Armour, Margaret Ann; Nakashima, Thomas T.
In: Journal of Organic Chemistry, Vol. 50, No. 19, 1985, p. 3516-3521.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranoses
AU - Yamamoto, Hiroshi
AU - Hanaya, Tadashi
AU - Kawamoto, Heizan
AU - Inokawa, Saburo
AU - Yamashita, Mitsuji
AU - Armour, Margaret Ann
AU - Nakashima, Thomas T.
PY - 1985
Y1 - 1985
N2 - Treatment of 3-O-acetyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D- xylofuranose (1c) with sodium dihydrobis(methoxyethoxy)aluminate, followed by the action of mineral acid and hydrogen peroxide, gave 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylopyranose (4a). The 3-O-benzyl derivative 4c was similarly obtained from the corresponding 3-O-benzyl-α-D-xylofuranose 1b. Diazotization of 3-O-acetyl-6-amino-5,6-dideoxy-5-C-(dimethoxyphosphinyl)-1,2-O-isopropylidene- α-D-glucofuranose (12), followed by hydrolysis and then treatment with chlorotriphenylmethane in pyridine, afforded the corresponding 5-deoxy-6-O-triphenylmethyl derivative 17. Similar ring enlargement of 17 exclusively yielded 5-deoxy-5-C-(hydroxyphosphinyl)-D-glucopyranose. The structures of these phosphorus sugar analogues were established on the basis of mass and 400-MHz 1H NMR spectra of the per-O-acetyl-5-deoxy-5-C-(methoxyphosphinyl) derivatives 6-9 and 21-25.
AB - Treatment of 3-O-acetyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D- xylofuranose (1c) with sodium dihydrobis(methoxyethoxy)aluminate, followed by the action of mineral acid and hydrogen peroxide, gave 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylopyranose (4a). The 3-O-benzyl derivative 4c was similarly obtained from the corresponding 3-O-benzyl-α-D-xylofuranose 1b. Diazotization of 3-O-acetyl-6-amino-5,6-dideoxy-5-C-(dimethoxyphosphinyl)-1,2-O-isopropylidene- α-D-glucofuranose (12), followed by hydrolysis and then treatment with chlorotriphenylmethane in pyridine, afforded the corresponding 5-deoxy-6-O-triphenylmethyl derivative 17. Similar ring enlargement of 17 exclusively yielded 5-deoxy-5-C-(hydroxyphosphinyl)-D-glucopyranose. The structures of these phosphorus sugar analogues were established on the basis of mass and 400-MHz 1H NMR spectra of the per-O-acetyl-5-deoxy-5-C-(methoxyphosphinyl) derivatives 6-9 and 21-25.
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M3 - Article
AN - SCOPUS:0000241132
VL - 50
SP - 3516
EP - 3521
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -