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【结 构 式】

【分子编号】39997

【品名】(3R,4R,5S)-5-(hydroxymethyl)tetrahydro-2,3,4-furantriol

【CA登记号】

【 分 子 式 】C5H10O5

【 分 子 量 】150.1314

【元素组成】C 40% H 6.71% O 53.28%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(X)

In an alternative procedure, reaction of L-arabinose (X) with cyanamide in the presence of ammonium hydroxide produced the cyclic isourea (XI). Subsequent cycloaddition of methyl propiolate (XII) to (XI) generated the fused pyrimidone system (XIII). After protection of the free hydroxyl groups of (XIII) as the dibenzoate ester (XIV), treatment with HCl in DMF furnished uridine derivative (XV). Dechlorination of (XV) employing Bu3SnH and AIBN afforded intermediate (VIII), which was treated with Lawesson's reagent to give the thiocarbonyl analogue (IX). Finally, sulfur displacement with concomitant benzoate ester hydrolysis employing methanolic ammonia at 100 C in a pressure bomb furnished the title compound.

1 Bryant, M.L.; Gosselin, G.; Imbach, J.-L. (CNRS (Centre National de la Recherche Scientifique); Novirio Pharmaceuticals Ltd.); beta-L-2'-Deoxy-nucleosides for the treatment of hepatitis B. WO 0009531 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 39996 [(2S,3R,5S)-3-(benzoyloxy)-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate C23H20N2O7 详情 详情
(IX) 40005 [(2S,3R,5S)-3-(benzoyloxy)-5-[2-oxo-4-thioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate C23H20N2O6S 详情 详情
(X) 39997 (3R,4R,5S)-5-(hydroxymethyl)tetrahydro-2,3,4-furantriol C5H10O5 详情 详情
(XI) 39998 (3aS,5S,6S,6aR)-2-amino-5-(hydroxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazol-6-ol C6H10N2O4 详情 详情
(XII) 19588 methyl propiolate 922-67-8 C4H4O2 详情 详情
(XIII) 39999 (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-6-one 3736-77-4 C9H10N2O5 详情 详情
(XIV) 40000 [(2S,3S,3aR,9aS)-3-(benzoyloxy)-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-2-yl]methyl benzoate C23H18N2O7 详情 详情
(XV) 40001 [(2S,3S,4S,5S)-3-(benzoyloxy)-4-chloro-5-[2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl]methyl benzoate C23H19ClN2O7 详情 详情
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