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【结 构 式】 
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【分子编号】57920 【品名】tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-6-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]hexanoate 【CA登记号】 |
【 分 子 式 】C25H44BNO6 【 分 子 量 】465.4385 【元素组成】C 64.51% H 9.53% B 2.32% N 3.01% O 20.62% |
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)The protected glutamic acid (I) is converted to the mixed anhydride (II) using ethyl chloroformate, and subsequently reduced to alcohol (III) by means of NaBH4. Swern oxidation of (III) provides aldehyde (IV), which is subjected to a Wittig condensation with triphenyl methylenephosphorane to afford olefin (V). Hydroboration of (V), followed by reaction with (+)-pinanediol (VI) leads to the boronate (VII). Finally, complete deprotection of (VII) with BCl3 yields the desired boronic acid.
| 【1】 Ash, D.E.; Carroll, P.J.; Baggio, R.; Cavalli, R.C.; Christianson, D.W.; Kanyo, Z.F.; Elbaum, D.; Inhibition of Mn2+2-arginase by borate leads to the design of a transition state analogue inhibitor, 2(S)-amino-6-boronohexanoic acid. J Am Chem Soc 1997, 119, 34, 8107. |
| 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) | 57915 | (4S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid | C14H25NO6 | 详情 | 详情 | |
| (II) | 57916 | C17H29NO8 | 详情 | 详情 | ||
| (III) | 57917 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-hydroxypentanoate | C14H27NO5 | 详情 | 详情 | |
| (IV) | 57918 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoate | C14H25NO5 | 详情 | 详情 | |
| (V) | 57919 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-hexenoate | C15H27NO4 | 详情 | 详情 | |
| (VI) | 16644 | (-)-Pinanediol; (1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol | 20536-52-1 | C10H18O2 | 详情 | 详情 |
| (VII) | 57920 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-6-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]hexanoate | C25H44BNO6 | 详情 | 详情 |
Extended Information