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【结 构 式】

【分子编号】53919

【品名】sodium (1R,2R)-1-(ethoxycarbonyl)-2-hydroxycyclopropanecarboxylate

【CA登记号】n/a

【 分 子 式 】C7H9NaO5

【 分 子 量 】196.135228

【元素组成】C 42.87% H 4.63% Na 11.72% O 40.79%

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:(V)

The selective hydrolysis of the ester group of the chiral cyclopropafuranone (I) with an excess of NaOH, followed by ring closing with HCl, gives the carboxylic acid (II), which is treated with ethyl chloroformate and TEA in THF to yield the mixed anhydride (III). The reduction of the anhydride group of (III) with NaBH4 in THF/water affords the chiral hydroxymethyl cyclopropafuranone (IV). Alternatively, the selective hydrolysis of the lactone group of (I) with 1 equivalent of NaOH provides the malonic hemiester hemi sodium salt (V), which is reduced with NaBH4 and cyclized with conc. HCl to give the already reported hydroxymethyl cyclopropafuranone (IV). The reaction of (IV) with Ms-Cl and TEA or with SOCl2 and TEA yields the mesyloxymethyl (VI) or the chloromethyl (VII) compounds, which are condensed with 2-amino-6-chloropurine (VIII) by means of K2CO3 in hot DMF to afford the adduct (IX). The hydrolysis of the chlorine atom of (IX) by means of HCOOH at 100 C provides the guanine derivative (X). Finally, the lactone group of (X) is reduced with NaBH4 in hot ethanol to give the target cyclopropane nucleoside.

1 Onishi, T.; et al.; A practical synthesis of antiviral cyclopropane nucleoside A-5021. Tetrahedron Lett 1999, 40, 50, 8845.
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) 38068 ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate C8H10O4 详情 详情
(II) 53916 (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid C6H6O4 详情 详情
(III) 53917   C8H8O6 详情 详情
(IV) 53918 (1S,5R)-1-(hydroxymethyl)-3-oxabicyclo[3.1.0]hexan-2-one C6H8O3 详情 详情
(V) 53919 sodium (1R,2R)-1-(ethoxycarbonyl)-2-hydroxycyclopropanecarboxylate n/a C7H9NaO5 详情 详情
(VI) 53920 [(5R)-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]methyl methanesulfonate C7H10O5S 详情 详情
(VII) 53921 (1R,5R)-1-(chloromethyl)-3-oxabicyclo[3.1.0]hexan-2-one C6H7ClO2 详情 详情
(VIII) 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
(IX) 53922 (1S,5R)-1-[(2-amino-6-chloro-9H-purin-9-yl)methyl]-3-oxabicyclo[3.1.0]hexan-2-one C11H10ClN5O2 详情 详情
(X) 53923 2-amino-9-{[(5R)-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]methyl}-1,9-dihydro-6H-purin-6-one C11H11N5O3 详情 详情
Extended Information