(Z,4S)-4-(acetyloxy)-2-pentenoic acid -Drug Synthesis Database

【结构式】

【分子编号】62113

【品名】(Z,4S)-4-(acetyloxy)-2-pentenoic acid

【CA登记号】

【分子式】C₇H₁₀O₄

【分子量】158.154

【元素组成】C 53.16% H 6.37% O 40.47%

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：(V)

Synthesis of the unsaturated acid precursor (V) is carried out as follows. Desilylation of 4-(trimethylsilyl)-3-butyn-2-ol (I) with tetrabutylammonium fluoride affords (II). The lithium acetylide generated from alkyne (II) is then carboxylated by CO2 to furnish the pentynoic acid derivative (III). Subsequent acetylation of the alcohol hydroxyl group of (III) leads to acetate ester (IV). Then, Lindlar hydrogenation of the triple bond gives rise to the cis alkene (V).

参考文献中间体

合成目标

【1】 Thompson, C.F.; Jamison, T.F; Jacobsen, E.N.; Total synthesis of FR901464. Convergent assembly of chiral componenents prepared by asymmetric catalysis. J Am Chem Soc 2000, 122, 45, 10482.

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)	62000	(2S)-4-(trimethylsilyl)-3-butyn-2-ol		C₇H₁₄OSi	详情	详情
(II)	13488	(2S)-3-Butyn-2-ol; (S)-(-)-3-Butyn-2-ol	2914-69-4	C₄H₆O	详情	详情
(III)	62111	(4S)-4-hydroxy-2-pentynoic acid		C₅H₆O₃	详情	详情
(IV)	62112	(4S)-4-(acetyloxy)-2-pentynoic acid		C₇H₈O₄	详情	详情
(V)	62113	(Z,4S)-4-(acetyloxy)-2-pentenoic acid		C₇H₁₀O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Acylation of amine (XXIX) with the unsaturated acid (V) in the presence of HBTU gives amide (XXX). Dehydroiodination of (XXX) by means of DBU in DMF leads to the exocyclic enol ether (XXXI). The O-silyl group of (XXXI) is then removed with tetrabutylammonium fluoride and acetic acid, to yield alcohol (XXXII). Finally, acid-catalyzed hydration of the cyclic enol ether (XXXII) in aqueous THF gives rise to the target hemiketal compound.

参考文献中间体

合成目标

【1】 Thompson, C.F.; Jamison, T.F; Jacobsen, E.N.; Total synthesis of FR901464. Convergent assembly of chiral componenents prepared by asymmetric catalysis. J Am Chem Soc 2000, 122, 45, 10482.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(V)	62113	(Z,4S)-4-(acetyloxy)-2-pentenoic acid	C₇H₁₀O₄	详情	详情
(XXIX)	62136	(2R,3R,5S,6S)-6-((2E,4E)-5-{(3R,4R,5R,7R)-7-(iodomethyl)-4-[(triethylsilyl)oxy]-1,6-dioxaspiro[2.5]oct-5-yl}-3-methyl-2,4-pentadienyl)-2,5-dimethyltetrahydro-2H-pyran-3-amine; (2R,3R,5S,6S)-6-((2E,4E)-5-{(3R,4R,5R,7R)-7-(iodomethyl)-4-[(triethylsilyl)oxy]-1,6-dioxaspiro[2.5]oct-5-yl}-3-methyl-2,4-pentadienyl)-2,5-dimethyltetrahydro-2H-pyran-3-ylamine	C₂₆H₄₆INO₄Si	详情	详情
(XXX)	62137	(1S,2Z)-4-{[(2R,3R,5S,6S)-6-((2E,4E)-5-{(3R,4R,5R,7R)-7-(iodomethyl)-4-[(triethylsilyl)oxy]-1,6-dioxaspiro[2.5]oct-5-yl}-3-methyl-2,4-pentadienyl)-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-1-methyl-4-oxo-2-butenyl acetate	C₃₃H₅₄INO₇Si	详情	详情
(XXXI)	62138	(1S,2Z)-4-{[(2R,3R,5S,6S)-2,5-dimethyl-6-((2E,4E)-3-methyl-5-{(3R,4R,5R)-7-methylene-4-[(triethylsilyl)oxy]-1,6-dioxaspiro[2.5]oct-5-yl}-2,4-pentadienyl)tetrahydro-2H-pyran-3-yl]amino}-1-methyl-4-oxo-2-butenyl acetate	C₃₃H₅₃NO₇Si	详情	详情
(XXXII)	62139	(1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R)-4-hydroxy-7-methylene-1,6-dioxaspiro[2.5]oct-5-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate	C₂₇H₃₉NO₇	详情	详情

Extended Information