ethyl 2-[[(2R)-2-{[(2R)-2-aminobutanoyl]amino}-3-(phenylselanyl)propanoyl](methyl)amino]acetate -Drug Synthesis Database

【结构式】

【分子编号】58844

【品名】ethyl 2-[[(2R)-2-{[(2R)-2-aminobutanoyl]amino}-3-(phenylselanyl)propanoyl](methyl)amino]acetate

【CA登记号】

【分子式】C₁₈H₂₇N₃O₄Se

【分子量】428.3902

【元素组成】C 50.47% H 6.35% N 9.81% O 14.94% Se 18.43%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XXVII)

The tripeptide building block (XXVII) is prepared as follows. Cyclization of N-Boc-L-serine (XIX) to the beta-lactone (XX) is achieved by treatment with DEAD and PPh3. Subsequent ring opening with diphenyldiselenide in the presence of a reducing agent leads to selenide (XXI). Aminoacid (XXI) is then coupled to sarcosine ethyl ester (XXII) to afford dipeptide (XXIII). After acidic Boc group cleavage in (XXIII), the resultant carboxylic acid (XXIV) is coupled to N-Boc-D-aminobutyric acid (XXV) to give (XXVI). The N-Boc group of (XXVI) is then deprotected with trifluoroacetic acid, producing intermediate (XXVII).

参考文献中间体

合成目标

【1】 Ley, S.V.; et al.; Total synthesis of the cyclic heptapeptide argyrin B: A new potent inhibitor of T-cell independent antibody formation. Org Lett 2002, 4, 5, 711.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIX)	20126	(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionic acid		C₈H₁₅NO₅	详情	详情
(XX)	58838	tert-butyl (3S)-2-oxooxetanylcarbamate		C₈H₁₃NO₄	详情	详情
(XXI)	58839	(2R)-2-[(tert-butoxycarbonyl)amino]-3-(phenylselanyl)propanoic acid		C₁₄H₁₉NO₄Se	详情	详情
(XXII)	32138	Sarcosine ethyl ester; Ethyl 2-(methylamino)acetate	52605-49-9	C₅H₁₁NO₂	详情	详情
(XXIII)	58840	ethyl 2-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(phenylselanyl)propanoyl](methyl)amino]acetate		C₁₉H₂₈N₂O₅Se	详情	详情
(XXIV)	58841	ethyl 2-[[(2R)-2-amino-3-(phenylselanyl)propanoyl](methyl)amino]acetate		C₁₄H₂₀N₂O₃Se	详情	详情
(XXV)	58842	(2R)-2-[(tert-butoxycarbonyl)amino]butanoic acid		C₉H₁₇NO₄	详情	详情
(XXVI)	58843	ethyl (6R,9R)-6-ethyl-2,2,11-trimethyl-4,7,10-trioxo-9-[(phenylselanyl)methyl]-3-oxa-5,8,11-triazatridecan-13-oate		C₂₃H₃₅N₃O₆Se	详情	详情
(XXVII)	58844	ethyl 2-[[(2R)-2-{[(2R)-2-aminobutanoyl]amino}-3-(phenylselanyl)propanoyl](methyl)amino]acetate		C₁₈H₂₇N₃O₄Se	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXVII)

Basic hydrolysis of the precursor tetrapeptide ester (XVIII) provides acid (XXVIII). This is then coupled to the tripeptide ester (XXVII), leading to the linear peptide precursor (XXIX). Sequential hydrolysis in (XXIX) of the ethyl ester group with LiOH and the N-Boc group with trifluoroacetic acid produces aminoacid (XXX).

参考文献中间体

合成目标

【1】 Ley, S.V.; et al.; Total synthesis of the cyclic heptapeptide argyrin B: A new potent inhibitor of T-cell independent antibody formation. Org Lett 2002, 4, 5, 711.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVIII)	58837	methyl 2-{[(2S)-2-{[(2S)-2-{[(2-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-1,3-thiazol-4-yl)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate	C₃₇H₄₃N₇O₈S	详情	详情
(XXVII)	58844	ethyl 2-[[(2R)-2-{[(2R)-2-aminobutanoyl]amino}-3-(phenylselanyl)propanoyl](methyl)amino]acetate	C₁₈H₂₇N₃O₄Se	详情	详情
(XXVIII)	58845	2-{[(2S)-2-{[(2S)-2-{[(2-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-1,3-thiazol-4-yl)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetic acid	C₃₆H₄₁N₇O₈S	详情	详情
(XXIX)	58846	ethyl (3S,6S,12R,15R)-1-(2-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-1,3-thiazol-4-yl)-12-ethyl-3-(1H-indol-3-ylmethyl)-6-[(4-methoxy-1H-indol-3-yl)methyl]-17-methyl-1,4,7,10,13,16-hexaoxo-15-[(phenylselanyl)methyl]-2,5,8,11,14,17-hexaazanonadecan-19-oate	C₅₄H₆₆N₁₀O₁₁SSe	详情	详情
(XXX)	58847	(3S,6S,12R,15R)-1-{2-[(1R)-1-aminoethyl]-1,3-thiazol-4-yl}-12-ethyl-3-(1H-indol-3-ylmethyl)-6-[(4-methoxy-1H-indol-3-yl)methyl]-17-methyl-1,4,7,10,13,16-hexaoxo-15-[(phenylselanyl)methyl]-2,5,8,11,14,17-hexaazanonadecan-19-oic acid	C₄₇H₅₄N₁₀O₉SSe	详情	详情

Extended Information