【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