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 - 1988/9/1
Y1 - 1988/9/1
N2 - Treatment of (RS)-3-O-acetyl-5-deoxy-5-(ethylmethoxyphosphinyl)-1,2-O-isopropyUdene-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 and4C1(L) conformations were established by spectroscopy.
AB - Treatment of (RS)-3-O-acetyl-5-deoxy-5-(ethylmethoxyphosphinyl)-1,2-O-isopropyUdene-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 and4C1(L) conformations were established by spectroscopy.
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U2 - 10.1021/jo00255a023
DO - 10.1021/jo00255a023
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 -