TY - JOUR
T1 - A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar
AU - Hanaya, Tadashi
AU - Tsukui, Hiroyuki
AU - Igi, Naomi
AU - Noguchi, Ayashi
AU - Kawamoto, Heizan
AU - Yamamoto, Hiroshi
PY - 2007/4/13
Y1 - 2007/4/13
N2 - The addition reaction of dimethyl phosphonate to (2R,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-1,3-dioxan-5-one (11a), followed by dehydroxylation, provided 1-O-(tert-butyldimethylsilyl)-3-deoxy-3-dimethoxy-phosphinoyl-2,4-O-ethylidene-d-erythritol (13a). Elongation of carbon skeleton of the d-erythrose (14) derived from 13a and then acidic methanolysis gave a mixture of methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-α,β-d-erythro-pentopyranosides (7), which was led to 2-deoxy-D-ribofuranose phospho sugar (4) in an appreciably improved total yield compared with the procedures via previously reported route.
AB - The addition reaction of dimethyl phosphonate to (2R,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-1,3-dioxan-5-one (11a), followed by dehydroxylation, provided 1-O-(tert-butyldimethylsilyl)-3-deoxy-3-dimethoxy-phosphinoyl-2,4-O-ethylidene-d-erythritol (13a). Elongation of carbon skeleton of the d-erythrose (14) derived from 13a and then acidic methanolysis gave a mixture of methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-α,β-d-erythro-pentopyranosides (7), which was led to 2-deoxy-D-ribofuranose phospho sugar (4) in an appreciably improved total yield compared with the procedures via previously reported route.
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U2 - 10.3987/COM-06-S(K)28
DO - 10.3987/COM-06-S(K)28
M3 - Article
AN - SCOPUS:34547840158
SN - 0385-5414
VL - 72
SP - 411
EP - 420
JO - Heterocycles
JF - Heterocycles
ER -