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【结 构 式】

【分子编号】35524

【品名】5-[2-(benzyloxy)ethyl]-1,3-dioxan-2-one

【CA登记号】

【 分 子 式 】C13H16O4

【 分 子 量 】236.26764

【元素组成】C 66.09% H 6.83% O 27.09%

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:(II)

Treatment of diol (I) with 1,1'-carbonyldiimidazole produced the cyclic carbonate (II). Cleavage of the O-benzyl group of (II) by hydrogenolysis over Pd/C, gave alcohol (III), which was converted to mesylate (IV) by means of MsCl and Et3N. Subsequent coupling of (IV) with 2-amino-6-chloropurine (V) produced the 9-alkylated derivative (VI). The chlorine atom of (VI) was then removed by hydrogenolysis in the presence of Pd/C and Et3N to furnish (VII). Finally, opening of the cyclic carbonate group of (VII) with isopropanol upon heating in the presence of silica gel yielded the target compound.

1 Kim, D.-K.; Lee, N.; Kim, Y.-W.; Chang, K.; Kim, J.S.; Im, G.J.; Choi, W.S.; Jung, I.; Kim, T.S.; Hwang, Y.Y.; Min, D.S.; Um, K.A.; Cho, Y.B.; Kim, K.H.; Synthesis and evaluation of 2-amino-9-(3-hydroxymethyl-4-alkoxycarbonyloxybut-1-yl)purines as potential prodrugs of penciclovir. J Med Chem 1998, 41, 18, 3435.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 35523 2-[2-(benzyloxy)ethyl]-1,3-propanediol C12H18O3 详情 详情
(II) 35524 5-[2-(benzyloxy)ethyl]-1,3-dioxan-2-one C13H16O4 详情 详情
(III) 35525 5-(2-hydroxyethyl)-1,3-dioxan-2-one C6H10O4 详情 详情
(IV) 35526 2-(2-oxo-1,3-dioxan-5-yl)ethyl methanesulfonate C7H12O6S 详情 详情
(V) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(VI) 35534 5-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-1,3-dioxan-2-one C11H12ClN5O3 详情 详情
(VII) 35527 5-[2-(2-amino-9H-purin-9-yl)ethyl]-1,3-dioxan-2-one C11H13N5O3 详情 详情
Extended Information