5-(benzyloxy)-4-[[(benzyloxy)carbonyl]amino]-5-oxopentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】29989

【品名】5-(benzyloxy)-4-[[(benzyloxy)carbonyl]amino]-5-oxopentanoic acid

【CA登记号】65706-99-2

【分子式】C₂₀H₂₁NO₆

【分子量】371.38988

【元素组成】C 64.68% H 5.7% N 3.77% O 25.85%

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：(III)

N-carbobenzyloxy-L-glutamic acid (I) is converted to the anhydride (II). Reaction of (II) with benzyl alcohol gives a mixture of half esters from which the halt ester (III) is isolated as the dicyclohexylamine salt. (III) is esterified with 4-nitrophenol (IV) with the aid of dicyclohexyl carbodiimide and the product (V) is reacted with taurine (VI). Deprotection of the resulting peptide (VII) by catalytic debenzylation affords glutaurine.

参考文献中间体

合成目标

【1】 Feuer, L.; et al. (Chinoin Pharmaceutical and Chemical Works Co., Ltd.); Method of preparing gamma-L-glutamyl taurine. US 4110441 .
【2】 Nogradi, M.; Glutaurine. Drugs Fut 1984, 9, 2, 110.

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)	29987	N-[(benzyloxy)carbonyl]glutamic acid	1155-62-0	C₁₃H₁₅NO₆	详情	详情
(II)	29988	benzyl 2,6-dioxotetrahydro-2H-pyran-3-ylcarbamate		C₁₃H₁₃NO₅	详情	详情
(III)	29989	5-(benzyloxy)-4-[[(benzyloxy)carbonyl]amino]-5-oxopentanoic acid	65706-99-2	C₂₀H₂₁NO₆	详情	详情
(IV)	11236	4-Nitrophenol; p-Nitrophenol	100-02-7	C₆H₅NO₃	详情	详情
(V)	29990	1-benzyl 5-(4-nitrophenyl) 2-[[(benzyloxy)carbonyl]amino]pentanedioate		C₂₆H₂₄N₂O₈	详情	详情
(VI)	29991	2-ammonio-1-ethanesulfonate		C₂H₇NO₃S	详情	详情
(VII)	29992	2-[(5-(benzyloxy)-4-[[(benzyloxy)carbonyl]amino]-5-oxopentanoyl)amino]-1-ethanesulfonic acid		C₂₂H₂₆N₂O₈S	详情	详情

Extended Information