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【结 构 式】

【分子编号】57916

【品名】 

【CA登记号】

【 分 子 式 】C17H29NO8

【 分 子 量 】375.4192

【元素组成】C 54.39% H 7.79% N 3.73% O 34.09%

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:(II)

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