allyl 2,5-dioxo-1-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】25730

【品名】allyl 2,5-dioxo-1-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₈H₉NO₄

【分子量】183.1638

【元素组成】C 52.46% H 4.95% N 7.65% O 34.94%

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)

A formal total synthesis of vancomycin has been reported. The known aglycon of vancomycin (I) was protected at the amino group as the allyloxy- carbonyl derivative (III) using allyloxycarbonyl succinimide (II). Then, carboxylate group was converted to allyl ester (V) with allyl bromide (IV) and KHCO3.

参考文献中间体

合成目标

【1】 Thompson, C.; et al.; Synthesis of vancomycin from the aglycon. J Am Chem Soc 1999, 121, 6, 1237.

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)	25729	(1S,2R,18R,19R,22S,25R,28R,40R)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37,50-hexahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylic acid		C₅₃H₅₂Cl₂N₈O₁₇	详情	详情
(II)	25730	allyl 2,5-dioxo-1-pyrrolidinecarboxylate		C₈H₉NO₄	详情	详情
(III)	25731	(1S,2R,18R,19R,22S,25R,28R,40R)-19-([(2R)-2-[[(allyloxy)carbonyl](methyl)amino]-4-methylpentanoyl]amino)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37,50-hexahydroxy-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylic acid		C₅₇H₅₆Cl₂N₈O₁₉	详情	详情
(IV)	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情
(V)	25732	allyl (1S,2R,18R,19R,22S,25R,28R,40R)-19-([(2R)-2-[[(allyloxy)carbonyl](methyl)amino]-4-methylpentanoyl]amino)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37,50-hexahydroxy-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(50),9,11,14,16,29(49),30,32,34,36,38,45,47-pentadecaene-40-carboxylate		C₆₀H₆₀Cl₂N₈O₁₉	详情	详情

Extended Information