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【结 构 式】

【分子编号】35329

【品名】2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]-3-(benzyloxy)propyl propionate

【CA登记号】

【 分 子 式 】C19H23N5O5

【 分 子 量 】401.42232

【元素组成】C 56.85% H 5.78% N 17.45% O 19.93%

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:(XXV)

The condensation of 1-acetoxy-2-(acetoxymethoxy)-3-(benzyloxy) propane (XXI) with guanine (XXII) by means of HMDS and trifluoromethanesulfonic acid gives O-acetyl-O'-benzylganciclovir (XXIII), which is deacetylated with NaOH in methanol to yield the previously reported mono-O-benzylganciclovir (XVIII). The preceding reaction sequence can also be performed by using 1-(benzyloxy)-2-(propionyloxymethoxy)-3-(propionyloxy)propane (XXIV) instead of compound (XXI), yielding intermediate (XXV) and finally the previously reported mono-O-benzylganciclovir (XVIII).

1 Sorbera, L.A.; Castañer, J.; Castañer, R.M.; Valganciclovir Hydrochloride. Drugs Fut 2000, 25, 5, 474.
2 Dvorak, C.A.; Beard, C.C.; Wren, D.L.; Axt, S.D.; Han, Y.-K.; Fatheree, P.R.; Nguyen, S.L.; Lund, J.P.; Fisher, L.E.; Arzeno, H.B.; Humphreys, E.R. (F. Hoffmann-La Roche AG); Process for preparing purine derivs.. US 6040446; WO 9727198 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVIII) 35324 2-amino-9-[[2-(benzyloxy)-1-(hydroxymethyl)ethoxy]methyl]-1,9-dihydro-6H-purin-6-one C16H19N5O4 详情 详情
(XXI) 35326 [2-(acetoxy)-1-[(benzyloxy)methyl]ethoxy]methyl acetate C15H20O6 详情 详情
(XXII) 10352 2-Amino-1,9-dihydro-6H-purin-6-one; Guanine 73-40-5 C5H5N5O 详情 详情
(XXIII) 35327 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]-3-(benzyloxy)propyl acetate C18H21N5O5 详情 详情
(XXIV) 35328 3-(benzyloxy)-2-[(propionyloxy)methoxy]propyl propionate C17H24O6 详情 详情
(XXV) 35329 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]-3-(benzyloxy)propyl propionate C19H23N5O5 详情 详情
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