ethyl (E,5S)-5,6-dihydroxy-2-hexenoate -Drug Synthesis Database

【结构式】

【分子编号】30102

【品名】ethyl (E,5S)-5,6-dihydroxy-2-hexenoate

【CA登记号】

【分子式】C₈H₁₄O₄

【分子量】174.19676

【元素组成】C 55.16% H 8.1% O 36.74%

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：(XVII)

In a related procedure, the chiral triol (XIII) was protected as the ketal (XIV), and then oxidized to aldehyde (XV). Subsequent Wittig condensation of (XV) with phosphorane (IV) afforded unsaturated ester (XVI). After ketal hydrolysis of (XVI), cyclization by means of I2 and NaHCO3 yielded cyclic ether (XVIII). Oxidation of (XVIII) to ketone (XIX) and cyclization in the presence of DBU produced bicyclic compound (XX). This was converted to the chiral spiro hydantoin (XXI) with KCN and (NH4)2CO3 and finally hydrolyzed with NaOH to give the corresponding dicarboxylic acid.

参考文献中间体

合成目标

【1】 Massey, S.M.; Monn, J.A.; Valli, M.J. (Eli Lilly and Company); Excitatory amino acid derivs.. US 5688826 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	14182	ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane	1099-45-2	C₂₂H₂₁O₂P	详情	详情
(XIII)	30098	(2S)-1,2,4-butanetriol; (S)-1,2,4-butanetriol	42890-76-6	C₄H₁₀O₃	详情	详情
(XIV)	30099	2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-ethanol		C₇H₁₄O₃	详情	详情
(XV)	30100	2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde		C₇H₁₂O₃	详情	详情
(XVI)	30101	ethyl (E)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-butenoate		C₁₁H₁₈O₄	详情	详情
(XVII)	30102	ethyl (E,5S)-5,6-dihydroxy-2-hexenoate		C₈H₁₄O₄	详情	详情
(XVIII)	30103	ethyl (2S)-2-[(2R,4S)-4-hydroxytetrahydro-2-furanyl]-2-iodoethanoate		C₈H₁₃IO₄	详情	详情
(XIX)	30104	ethyl (2S)-2-iodo-2-[(2R)-4-oxotetrahydro-2-furanyl]ethanoate		C₈H₁₁IO₄	详情	详情
(XX)	30105	ethyl (1R,5R)-4-oxo-2-oxabicyclo[3.1.0]hexane-6-carboxylate		C₈H₁₀O₄	详情	详情
(XXI)	30106	(1'R,4S,5'S,6'S)-2,5-Dioxospiro[imidazolidine-4,4'-[2]oxabicyclo[3,1,0]hexane]-6'-carboxylic acid ethyl ester		C₁₀H₁₂N₂O₅	详情	详情

Extended Information