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【结 构 式】

【分子编号】52986

【品名】(2R)-2-{[2-amino-6-(benzyloxy)-9H-purin-9-yl]methyl}-4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)oxy]butyl stearate

【CA登记号】n/a

【 分 子 式 】C48H70N6O7

【 分 子 量 】843.12004

【元素组成】C 68.38% H 8.37% N 9.97% O 13.28%

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:(XXXIX)

In a further procedure, the prochiral diol (XX) was converted to the asymmetric mono-stearate ester (XXXII) employing vinyl stearate (XXXI) and lipase PS 30. After tosylation of alcohol (XXXII), the resulting diethoxy acetal (XXXIII) was hydrolyzed to aldehyde (XXXIV) employing different acidic catalysts. Reduction of aldehyde (XXXIV) to the corresponding alcohol (XXXV) was effected by means of catalytic hydrogenation over Ra-Ni or borane-tert-butylamine complex. Alcohol (XXXV) was further condensed with N-Cbz-L-valine (XVI), producing the diester tosylate (XXXVI). The analogous N-Boc- and N-Alloc-protected valine esters were similarly prepared. 6-Benzyloxy-2-aminopurine (XXXVII) was prepared by treatment of chloropurine (I) with benzyl alcohol and NaH or NaOH. Alkylation of purine (XXXVII) with tosylate (XXXVI) furnished adduct (XXXVIII), which was finally deprotected by catalytic hydrogenation. Optionally, tosylate (XXXVI) was condensed with chloropurine (I) to give (XXXIX). Hydrolysis of the chloropurine ring of (XXXIX) to the guanine derivative (XIII) employing either Et3N or HOAc, followed by catalytic hydrogenation as above, provided an alternative access to the title compound.

1 Synthesis of acyclic nucleoside derivs.. WO 9834917 .
2 Synthesis of acyclic nucleoside derivs.. WO 0008025 .
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) 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
(XIII) 52965 (2R)-2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)oxy]butyl stearate C41H64N6O7 详情 详情
(XVI) 18092 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutyric acid C13H17NO4 详情 详情
(XX) 52969 2-(2,2-Diethoxyethyl)-1,3-propanediol; 2-Hydroxymethyl-4,4-diethoxybutanol 55387-85-4 C9H20O4 详情 详情
(XXXI) 52979 vinyl stearate 111-63-7 C20H38O2 详情 详情
(XXXII) 52980 (2R)-4,4-diethoxy-2-(hydroxymethyl)butyl stearate n/a C27H54O5 详情 详情
(XXXIII) 52981 (2S)-4,4-diethoxy-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)butyl stearate n/a C34H60O7S 详情 详情
(XXXIV) 52982 (2S)-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)-4-oxobutyl stearate n/a C30H50O6S 详情 详情
(XXXV) 52983 (2S)-4-hydroxy-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)butyl stearate n/a C30H52O6S 详情 详情
(XXXVI) 52984 (2S)-4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)oxy]-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)butyl stearate n/a C43H67NO9S 详情 详情
(XXXVII) 14383 6-(benzyloxy)-9H-purin-2-ylamine; 6-(benzyloxy)-9H-purin-2-amine 19916-73-5 C12H11N5O 详情 详情
(XXXVIII) 52985 (2R)-2-[(2-amino-6-chloro-9H-purin-9-yl)methyl]-4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)oxy]butyl stearate n/a C41H63ClN6O6 详情 详情
(XXXIX) 52986 (2R)-2-{[2-amino-6-(benzyloxy)-9H-purin-9-yl]methyl}-4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)oxy]butyl stearate n/a C48H70N6O7 详情 详情
Extended Information