tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoate -Drug Synthesis Database

【结构式】

【分子编号】57918

【品名】tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoate

【CA登记号】

【分子式】C₁₄H₂₅NO₅

【分子量】287.35624

【元素组成】C 58.52% H 8.77% N 4.87% O 27.84%

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：(IV)

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.

参考文献中间体

合成目标

【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