benzyl 3-oxotetradecanoate -Drug Synthesis Database

【结构式】

【分子编号】59106

【品名】benzyl 3-oxotetradecanoate

【CA登记号】

【分子式】C₂₁H₃₂O₃

【分子量】332.48328

【元素组成】C 75.86% H 9.7% O 14.44%

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：(XLI)

Keto ester (XLI) was obtained by Reformatskii condensation of the organozinc reagent generated from benzyl bromoacetate (XL) with n-undecyl cyanide (XXXIX). Subsequent hydrogenolysis of the benzyl ester of (XLI) in the presence of Pearlman's catalyst furnished keto acid (XLII). Acylation of the diamino compound (XXXVIII) with ketoacid (XLII), by means of DCC, provided diamide (XLIII). Then, desilylation of (XLIII) to afford alcohol (XLIV) was accomplished employing HF in acetonitrile.

参考文献中间体

合成目标

【1】 Christ, W.J.; Kawata, T.; Hawkins, L.D.; Kobayashi, S.; Asano, O.; Rossignol, D.P. (Eisai Co., Ltd.); Anti-endotoxin cpds.. EP 0536969; JP 1993194470; US 5530113 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXXVIII)	59104	(1R)-1-(2-{[(2R,3R,4R,5S,6R)-2-[((2R,3S,4R,5R,6S)-3-{[(allyloxy)carbonyl]oxy}-4-[((3R)-3-{[(allyloxy)carbonyl]oxy}decyl)oxy]-5-amino-6-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-2-yl)methoxy]-3-amino-5-{[bis(allyloxy)phosphoryl]oxy}-6-(methoxymethyl)tetrahydro-2H-pyran-4-yl]oxy}ethyl)octyl (Z)-5-dodecenoate		C₆₅H₁₁₇N₂O₁₉PSi	详情	详情
(XXXIX)	59105	lauronitrile		C₁₂H₂₃N	详情	详情
(XL)	12869	benzyl 2-bromoacetate	5437-45-6	C₉H₉BrO₂	详情	详情
(XLI)	59106	benzyl 3-oxotetradecanoate		C₂₁H₃₂O₃	详情	详情
(XLII)	59107	3-oxotetradecanoic acid		C₁₄H₂₆O₃	详情	详情
(XLIII)	59108	(1R)-1-[2-({(2R,3R,4R,5S,6R)-2-({(2R,3S,4R,5R,6S)-3-{[(allyloxy)carbonyl]oxy}-4-[((3R)-3-{[(allyloxy)carbonyl]oxy}decyl)oxy]-6-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-2-yl}methoxy)-5-{[bis(allyloxy)phosphoryl]oxy}-6-(methoxymethyl)-3-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-4-yl}oxy)ethyl]octyl (Z)-5-dodecenoate		C₉₃H₁₆₅N₂O₂₃PSi	详情	详情
(XLIV)	59109	(1R)-1-[2-({(2R,3R,4R,5S,6R)-2-({(2R,3S,4R,5R)-3-{[(allyloxy)carbonyl]oxy}-4-[((3R)-3-{[(allyloxy)carbonyl]oxy}decyl)oxy]-6-hydroxy-5-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-2-yl}methoxy)-5-{[bis(allyloxy)phosphoryl]oxy}-6-(methoxymethyl)-3-[(3-oxotetradecanoyl)amino]tetrahydro-2H-pyran-4-yl}oxy)ethyl]octyl (Z)-5-dodecenoate		C₈₇H₁₅₁N₂O₂₃P	详情	详情

Extended Information