【结 构 式】 |
【分子编号】30106 【品名】(1'R,4S,5'S,6'S)-2,5-Dioxospiro[imidazolidine-4,4'-[2]oxabicyclo[3,1,0]hexane]-6'-carboxylic acid ethyl ester 【CA登记号】 |
【 分 子 式 】C10H12N2O5 【 分 子 量 】240.21576 【元素组成】C 50% H 5.04% N 11.66% O 33.3% |
合成路线1
该中间体在本合成路线中的序号:(XXI)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.
【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 |