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【结 构 式】

【分子编号】10352

【品名】2-Amino-1,9-dihydro-6H-purin-6-one; Guanine

【CA登记号】73-40-5

【 分 子 式 】C5H5N5O

【 分 子 量 】151.1278

【元素组成】C 39.74% H 3.33% N 46.34% O 10.59%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(I)

An efficient and selective process for the synthesis of acyclovir has been published: The reaction of guanine (I) with refluxing hexamethyldisilazane (HMDS) (II) by means of trifluoromethanesulfonic acid, elimination of the HMDS in excess and condensation of the resulting product with refluxing 1,3-dioxolane (III) gives 9-[2-(trimethylsilyloxy)ethoxymethyl]guanine (IV), which is finally hydrolyzed with refluxing acetic acid/water.

1 Han, Y.-K.; Harrington, P.J.; Schloemer, G.C. (F. Hoffmann-La Roche AG); Preparation of acyclovir. EP 0709385; JP 1996053451 .
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) 10352 2-Amino-1,9-dihydro-6H-purin-6-one; Guanine 73-40-5 C5H5N5O 详情 详情
(III) 10353 1,3-Dioxalane; 1,3-Dioxolane 646-06-0 C3H6O2 详情 详情
(IV) 10354 2-Amino-9-([2-[(trimethylsilyl)oxy]ethoxy]methyl)-1,9-dihydro-6H-purin-6-one C11H19N5O3Si 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

The acetylation of guanine (I) or guanosine (II) with acetic anhydride gives the diacetyl guanine (III), which is condensed with 1,4-diacetoxy-2-oxabutane (IV) by means of TsOH to yield N,O-diacetyl acyclovir (V). Finally, this compound is deacetylated with NH3, NaOH or pyrrolidine at room temperature, or also with refluxing glycol.

1 Gao, H.; Mitra, A.K.; Synthesis of acyclovir, ganciclovir and their prodrugs: A review. Synthesis 2000, 3, 329.
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) 10352 2-Amino-1,9-dihydro-6H-purin-6-one; Guanine 73-40-5 C5H5N5O 详情 详情
(II) 38958 Guanosine; 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,9-dihydro-6H-purin-6-one 118-00-3 C10H13N5O5 详情 详情
(III) 29161 N-(9-acetyl-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide; N2,9-Diacetylguanine 3056-33-5 C9H9N5O3 详情 详情
(IV) 46052 [2-(acetoxy)ethoxy]methyl acetate C7H12O5 详情 详情
(V) 10784 2-[[2-(acetamido)-6-oxo-1,6-dihydro-9H-purin-9-yl]methoxy]ethyl acetate; Acetic acid 2-(2-acetamido-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester 75128-73-3 C12H15N5O5 详情 详情

合成路线3

该中间体在本合成路线中的序号:(XXII)

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
Extended Information