Abstract
Treatment of (5RS)-3-O-acetyl-5-deoxy-5-(ethylmethoxyphosphinyl)-1,2-O-isopropylidene-α -D-xylo-hexofuranose (5) with dihydropyran in dichloromethane containing pyridinium p-toluenesulfonate gave the 6-O-(tetrahydropyran-2-yl) derivative 7 in 90% yield. Reduction of 7 with sodium dihydrobis(2-methoxyethoxy)aluminate followed by acid hydrolysis preponderantly provided the title compounds, the first unsubstituted L-idopyranoses having a phosphinyl group in the hemiacetal ring. These compounds were converted into four separable 1,2,3,4,6-penta-O-acetates 11a-d, whose structures and 4C1 (L) conformations were established by spectroscopy.
| Original language | English |
|---|---|
| Pages (from-to) | 4790-4793 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 53 |
| Issue number | 20 |
| Publication status | Published - 1988 |
Fingerprint
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis and structural analysis of 5-deoxy-5-[(RS)-ethylphosphinyl]-α,β-L-idopyranoses. / Yamamoto, Hiroshi; Hanaya, Tadashi; Kawamoto, Heizan; Inokawa, Saburo.
In: Journal of Organic Chemistry, Vol. 53, No. 20, 1988, p. 4790-4793.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and structural analysis of 5-deoxy-5-[(RS)-ethylphosphinyl]-α,β-L-idopyranoses
AU - Yamamoto, Hiroshi
AU - Hanaya, Tadashi
AU - Kawamoto, Heizan
AU - Inokawa, Saburo
PY - 1988
Y1 - 1988
N2 - Treatment of (5RS)-3-O-acetyl-5-deoxy-5-(ethylmethoxyphosphinyl)-1,2-O-isopropylidene-α -D-xylo-hexofuranose (5) with dihydropyran in dichloromethane containing pyridinium p-toluenesulfonate gave the 6-O-(tetrahydropyran-2-yl) derivative 7 in 90% yield. Reduction of 7 with sodium dihydrobis(2-methoxyethoxy)aluminate followed by acid hydrolysis preponderantly provided the title compounds, the first unsubstituted L-idopyranoses having a phosphinyl group in the hemiacetal ring. These compounds were converted into four separable 1,2,3,4,6-penta-O-acetates 11a-d, whose structures and 4C1 (L) conformations were established by spectroscopy.
AB - Treatment of (5RS)-3-O-acetyl-5-deoxy-5-(ethylmethoxyphosphinyl)-1,2-O-isopropylidene-α -D-xylo-hexofuranose (5) with dihydropyran in dichloromethane containing pyridinium p-toluenesulfonate gave the 6-O-(tetrahydropyran-2-yl) derivative 7 in 90% yield. Reduction of 7 with sodium dihydrobis(2-methoxyethoxy)aluminate followed by acid hydrolysis preponderantly provided the title compounds, the first unsubstituted L-idopyranoses having a phosphinyl group in the hemiacetal ring. These compounds were converted into four separable 1,2,3,4,6-penta-O-acetates 11a-d, whose structures and 4C1 (L) conformations were established by spectroscopy.
UR - http://www.scopus.com/inward/record.url?scp=0023691605&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0023691605&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0023691605
VL - 53
SP - 4790
EP - 4793
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -