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【结 构 式】 
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【分子编号】65699 【品名】 【CA登记号】 |
【 分 子 式 】C12H18O3 【 分 子 量 】210.27312 【元素组成】C 68.55% H 8.63% O 22.83% |
合成路线1
该中间体在本合成路线中的序号：(XXIV)The preparation of the hydroxylated adamantane (IV) is shown in Scheme 3. 1-Adamantyl bromide (XXII) is condensed with 1,1,2-tris(trimethylsilyloxy)ethylene (XXIII) by means of ZnCl2 in CH2Cl2 to afford the adamantylglycolic acid (XXIV), which is esterified to (XXV) utilizing a solution of acetyl chloride in MeOH. After Swern oxidation of (XXV) to the corresponding keto ester (XXVI), hydroxylation of the adamantane ring by means of HNO3/H2SO4 provides (XXVII). Alkaline hydrolysis of ester (XXVII) leads to the oxoacetic acid (XXVIII), which is converted to the target (S)-amino acid (IV) by reductive amination with phenylalanine dehydrogenase (3).
| 【3】 Politino, M., Cadin, M.M., Skonezny, P.M., Chen, J.G. (Bristol-Myers Squibb Co.). EP 1737970, JP 2007532137, WO 2005106011. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 65681 | (S)-(3-hydroxyadamantyl)glycine | C12H19NO3 | 详情 | 详情 | |
| (XXII) | 65698 | 1-Bromoadamantane; 1-Bromotricyclo[3.3.1.1(3,7)]decane; 1-Adamantyl bromide | 768-90-1 | C10H15Br | 详情 | 详情 |
| (XXIII) | 14534 | 2,2,7,7-tetramethyl-4-[(trimethylsilyl)oxy]-3,6-dioxa-2,7-disila-4-octene; 1,2-bis[(trimethylsilyl)oxy]vinyl trimethylsilyl ether; TRIS(TRIMETHYLSILYLOXY)ETHYLENE | 69097-20-7 | C11H28O3Si3 | 详情 | 详情 |
| (XXIV) | 65699 | C12H18O3 | 详情 | 详情 | ||
| (XXV) | 65700 | C13H20O3 | 详情 | 详情 | ||
| (XXVI) | 65701 | C13H18O3 | 详情 | 详情 | ||
| (XXVII) | 65702 | Methyl 2-(3-Hydroxy-1-adamantyl)-2-oxoacetate | C13H18O4 | 详情 | 详情 | |
| (XXVIII) | 65703 | 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid; 3-Hydroxy-alpha-oxotricyclo[3.3.1.1(3,7)]decane-1-acetic acid; | 709031-28-7 | C12H16O4 | 详情 | 详情 |