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【结 构 式】 
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【分子编号】57578 【品名】tert-butyl 2-{2-[2-({1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2-oxo-1,2-dihydro-4-pyrimidinyl}amino)-2-oxoethoxy]ethoxy}ethylcarbamate 【CA登记号】 |
【 分 子 式 】C20H32N4O10 【 分 子 量 】488.49504 【元素组成】C 49.18% H 6.6% N 11.47% O 32.75% |
合成路线1
该中间体在本合成路线中的序号：(XV)The Boc-protected amino alcohol (VIII) is condensed with ethyl bromoacetate (IX) in the presence of potassium tert-butoxide to afford ether (X). After alkaline hydrolysis of the ethyl ester group of (X), the resultant carboxylic acid (XI) is activated as the thioimide (XIII) upon treatment with thiazolidine-2-thione (XII) and EDC. Coupling of the acyl thiazolidinone (XIII) with cytosine arabinoside (XIV) leads to the N-acyl cytosine derivative (XV). The Boc protecting group of (XV) is then removed under acidic conditions to furnish amine (XVI).
| 【1】 Choe, Y.H.; et al.; Anticancer drug delivery systems: multi-loaded N-4-acyl poly(ethylene glycol) prodrugs of ara-C. II. Efficacy in ascites and solid tumors. J Control Release 2002, 79, 1-3, 55. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 57574 | tert-butyl 2-(2-hydroxyethoxy)ethylcarbamate | C9H19NO4 | 详情 | 详情 | |
| (IX) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (X) | 57575 | ethyl 2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-oate | C13H25NO6 | 详情 | 详情 | |
| (XI) | 57576 | 2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-oic acid | C11H21NO6 | 详情 | 详情 | |
| (XII) | 54751 | Thiazolidine-2-thione | C3H5NS2 | 详情 | 详情 | |
| (XIII) | 57577 | tert-butyl 2-{2-[2-oxo-2-(2-thioxo-1,3-thiazolidin-3-yl)ethoxy]ethoxy}ethylcarbamate | C14H24N2O5S2 | 详情 | 详情 | |
| (XIV) | 32709 | Cytarabine; Cytosine Beta-D-Arabinofuranoside; 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone | 147-94-4 | C9H13N3O5 | 详情 | 详情 |
| (XV) | 57578 | tert-butyl 2-{2-[2-({1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2-oxo-1,2-dihydro-4-pyrimidinyl}amino)-2-oxoethoxy]ethoxy}ethylcarbamate | C20H32N4O10 | 详情 | 详情 | |
| (XVI) | 57579 | 2-[2-(2-aminoethoxy)ethoxy]-N-{1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2-oxo-1,2-dihydro-4-pyrimidinyl}acetamide | C15H24N4O8 | 详情 | 详情 |