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【结 构 式】

【分子编号】30331

【品名】Hydrobenzoin; 1,2-diphenyl-1,2-ethanediol

【CA登记号】655-48-1

【 分 子 式 】C14H14O2

【 分 子 量 】214.26396

【元素组成】C 78.48% H 6.59% O 14.93%

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:(XIV)

The reduction of benzoin (XIII) with NaBH4 in ethanol/water gives the diol (XIV), which by a pinacol rearrangement by means of H2SO4 in hot acetic acid yields the diphenylacetaldehyde (XXV). The cyclization of (XV) with methyl vinyl ketone (XVI) by means of KOH in ethanol affords the cyclohexenone (XVII), which is reduced first with H2 over Pd/C in THF and then with NaBH4 in ethanol/water giving the 4,4-diphenylcyclohexanol (IX). The reaction of (IX) with PCl3 in THF yields the dichlorophosphite (XVIII), which is treated with imidazole (XIX) in THF affording the bis imidophosphite (XX). The condensation of (XX) with the previously obtained penta tert-butyl acetate compound (VI) in THF/heptane gives the imidophosphite (XXI), which is oxidized with sodium periodate yielding the phosphoric acid diester (XXII). Finally, the hydrolysis of (XXII) with HCl in ether/water eliminates the tert-butyl groups affording the desired chelating ligand (XII).

1 Amedio, J.C. Jr.; et al.; A practical preparation of 4,4-diphenylcyclohexanol: A key intermediate in the synthesis of MS-325. Synth Commun 1998, 28, 20, 3895.
2 Dunham, S.O.; Lauffer, R.B. (Epix Medical, Inc.); Contrast-enhanced diagnostic imaging method for monitoring interventional therapies. WO 9917809 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 30317 3,6,9-Tris(tert-butoxycarbonylmethyl)-4(R)-(hydroxymethyl)-3,6,9-triazaundecanedioic acid di-tert-butyl ester C35H65N3O11 详情 详情
(IX) 30319 4,4-diphenylcyclohexanol C18H20O 详情 详情
(XII) 30322 3,6,9-Tris(carboxymethyl)-4(R)-[4,4-diphenylcyclohexyloxy(hydroxy)phosphoryloxymethyl]-3,6,9-triazaundecanedioic acid C33H44N3O14P 详情 详情
(XIII) 24135 2-hydroxy-1,2-diphenyl-1-ethanone; benzoin 579-44-2 C14H12O2 详情 详情
(XIV) 30331 Hydrobenzoin; 1,2-diphenyl-1,2-ethanediol 655-48-1 C14H14O2 详情 详情
(XV) 30323 2,2-diphenylacetaldehyde 947-91-1 C14H12O 详情 详情
(XVI) 30324 3-buten-2-one; methyl vinyl ketone 78-94-4 C4H6O 详情 详情
(XVII) 30325 4,4-diphenyl-2-cyclohexen-1-one C18H16O 详情 详情
(XVIII) 30326 Dichlorophosphorous acid 4,4-diphenylcyclohexyl ester C18H19Cl2OP 详情 详情
(XIX) 10255 Imidazole; 1H-Imidazole 288-32-4 C3H4N2 详情 详情
(XX) 30327 4,4-diphenylcyclohexyl di(1H-imidazol-1-yl)phosphinite C24H25N4OP 详情 详情
(XXI) 30328 3,6,9-Tris(tert-butoxycarbonylmethyl)-4(R)-[4,4-diphenylcyclohexyloxy(1-imidazolyl)phosphoryloxymethyl]-3,6,9-triazaundecanedioic acid di-tert-butyl ester C56H86N5O12P 详情 详情
(XXII) 30329 3,6,9-Tris(tert-butoxycarbonylmethyl)-4(R)-[4,4-diphenylcyclohexyloxy(hydroxy)phosphoryloxymethyl]-3,6,9-triazaundecanedioic acid di-tert-butyl ester C53H84N3O14P 详情 详情
Extended Information