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【结 构 式】

【分子编号】68194

【品名】(2S,3R,5S)-5-(2-(2-(4-(tert-butyl)phenoxy)acetamido)-6-oxo-1H-purin-9(6H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl 2-(4-(tert-butyl)phenoxy)acetate

【CA登记号】 

【 分 子 式 】C34H41N5O8

【 分 子 量 】647.728

【元素组成】C 63.05% H 6.38% N 10.81% O 19.76%

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:(VII)

In one method, condensation of decitabine (I) with N,N-dimethylformamide dimethylacetal (II) gives the formamidine derivative (III), which by enzymatic acetylation with vinyl acetate in the presence of immobilized lipozyme in acetonitrile/1,4-dioxane yields the primary acetate (IV). Condensation of the deoxyribofuranose derivative (IV) with 2-cyanoethyl N,N,N’,N’-tetraisopropylphosphorodiamidate (V) in CH2Cl2 provides the phosphorodiamidate (VI), which then condenses with the deoxyguanosine derivative (VII) in CH2Cl2 to afford the trisubstituted phosphite (VIII) . oxidation of phosphite (VIII) with t-BuOOH provides the corresponding phosphate (IX), which is fully deprotected by means of NH3 in MeOH, and finally salified using naoAc in H2O/EtoH .

1 Redkar, S. Scaleup and development of a process for a low-volume subcutaneous formulation of SGI-110, a potent hypomethylating agent. 103rd Annu Meet Am Assoc Cancer Res (AACR) (March 31-April 4, Chicago) 2012, Abst.
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) 68188 decitabine;2-Desoxy-5-azacytidine;2'-Deoxy-5-azacytidine;5-Aza-2'-deoxycytidine;5-Azadeoxycytidine;Dacogen;1,3,5-Triazin-2(1H)-one,4-amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-;b-decitabine;s-Triazin-2(1H)-one,4-amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-(7CI,8CI) 2353-33-5 C8H12N4O4 详情 详情
(II) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情
(III) 68189 (Z)-N'-(5-((2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-oxo-4,5-dihydro-1,3,5-triazin-2-yl)-N,N-dimethylformimidamide   C11H17N5O4 详情 详情
(IV) 68190 ((2S,3R,5S)-5-(4-((Z)-((dimethylamino)methylene)amino)-2-oxo-1,3,5-triazin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl acetate   C13H19N5O5 详情 详情
(V) 48656 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphoramidite; 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite; Bis(diisopropylamino)-2-cyanoethoxyphosphine 102691-36-1 C15H32N3OP 详情 详情
(VI) 68191 ((2S,3R,5S)-3-(((2-cyanoethoxy)(diisopropylamino)phosphino)oxy)-5-(4-((Z)-((dimethylamino)methylene)amino)-2-oxo-1,3,5-triazin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate   C22H36N7O6P 详情 详情
(VII) 68194 (2S,3R,5S)-5-(2-(2-(4-(tert-butyl)phenoxy)acetamido)-6-oxo-1H-purin-9(6H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl 2-(4-(tert-butyl)phenoxy)acetate   C34H41N5O8 详情 详情
(VIII) 68193 (2S,3R,5S)-2-((((((2S,3R,5S)-2-(acetoxymethyl)-5-(4-((Z)-((dimethylamino)methylene)amino)-2-oxo-1,3,5-triazin-1(2H)-yl)tetrahydrofuran-3-yl)oxy)(2-cyanoethoxy)phosphino)oxy)methyl)-5-(2-(2-(4-(tert-butyl)phenoxy)acetamido)-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3-yl 2-(4-(tert-butyl)phenoxy)acetate   C50H62N11O14P 详情 详情
(IX) 68192 (2S,3R,5S)-2-((((((2S,3R,5S)-2-(acetoxymethyl)-5-(4-((Z)-((dimethylamino)methylene)amino)-2-oxo-1,3,5-triazin-1(2H)-yl)tetrahydrofuran-3-yl)oxy)(2-cyanoethoxy)phosphoryl)oxy)methyl)-5-(2-(2-(4-(tert-butyl)phenoxy)acetamido)-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3-yl 2-(4-(tert-butyl)phenoxy)acetate   C50H62N11O15P 详情 详情
Extended Information