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【结 构 式】

【分子编号】59857

【品名】(2R)-2-[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-hydroxyethyl 4-methylbenzenesulfonate

【CA登记号】

【 分 子 式 】C16H22O6S

【 分 子 量 】342.41308

【元素组成】C 56.12% H 6.48% O 28.04% S 9.36%

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:(IX)

A different synthetic strategy used 3,4:5,6-O-diisopropylidene-D-mannitol (VI) as the starting material. Dehydration of (VI) by means of dimethylformamide dimethylacetal and Ac2O provided olefin (VII). Selective hydrolysis of the terminal acetonide of (VII) was achieved by means of 80% AcOH to afford diol (VIII). Conversion of (VIII) to the primary tosylate (IX), followed by treatment with Na2CO3 gave epoxide (X). Oxirane ring opening in (X) with NaCN furnished the beta-hydroxy nitrile (XI). This was then protected as the unsymmetric acetal (XII) by acid-catalyzed addition of ethyl vinyl ether. Partial reduction of the nitrile function of (XII) with DIBAL in toluene at -78 C gave rise to aldehyde (XIII), which was further derivatized as the corresponding oxime (XIV). The nitrile oxide generated by treatment of oxime (XIV) with NaOCl and Et3N underwent a dipolar cycloaddition to the olefin, leading to isoxazoline (XV)

1 Takahashi, T.; Shiono, M. (Kuraray Co., Ltd.); Cyclohexanetriol derivs.. EP 0503630 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 18762 1-Ethoxyethylene; Ethyl vinyl ether;Ethoxyethene 109-92-2 C4H8O 详情 详情
(VI) 59854   C12H22O6 详情 详情
(VII) 59855   C12H20O4 详情 详情
(VIII) 59856 (1R)-1-[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1,2-ethanediol C9H16O4 详情 详情
(IX) 59857 (2R)-2-[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-hydroxyethyl 4-methylbenzenesulfonate C16H22O6S 详情 详情
(X) 59858 (4R,5R)-2,2-dimethyl-4-[(2R)oxiranyl]-5-vinyl-1,3-dioxolane C9H14O3 详情 详情
(XI) 59859 (3R)-3-[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-3-hydroxypropanenitrile C10H15NO3 详情 详情
(XII) 59860 (3R)-3-[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-3-(1-ethoxyethoxy)propanenitrile C14H23NO4 详情 详情
(XIII) 59861 (3R)-3-[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-3-(1-ethoxyethoxy)propanal C14H24O5 详情 详情
(XIV) 59862 (3R)-3-[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-3-(1-ethoxyethoxy)propanal oxime C14H25NO5 详情 详情
(XV) 59863 (3aR,4R,8bR)-2,2-dimethyl-3a,4,5,8,8a,8b-hexahydro[1,3]dioxolo[4,5-e][2,1]benzisoxazol-4-yl 1-ethoxyethyl ether; (3aR,4R,8bR)-4-(1-ethoxyethoxy)-2,2-dimethyl-3a,4,5,8,8a,8b-hexahydro[1,3]dioxolo[4,5-e][2,1]benzisoxazole C14H23NO5 详情 详情
Extended Information