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【结 构 式】

【分子编号】53249

【品名】iodo(octyl)zinc

【CA登记号】n/a

【 分 子 式 】C8H17IZn

【 分 子 量 】305.51745

【元素组成】C 31.45% H 5.61% I 41.54% Zn 21.4%

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:(II)

A new synthesis of FTY-720 has been reported: Condensation of 4-chlorobenzaldehyde (I) with octylzinc iodide (II) by means of Ni(0) gives 4-octylbenzaldehyde (III), which is treated with vinylmagnesium bromide (IV) to yield the allyl alcohol (V). Epoxidation of (V) with MCPBA affords the epoxide (VI), which is opened by means of NaNO2 and MgSO4 in refluxing methanol to provide 3-nitro-1-(4-octylphenyl)propane-1,2-diol (VII). Reaction of diol (VII) with trimethylsilyl chloride and NaI in acetonitrile gives 3-nitro-1-(4-octylphenyl)-1-propene (VIII), which is hydrogenated with H2 over Pd/C in ethanol yielding the corresponding nitropropane derivative (IX). The bis-formylation of compound (IX) with aqueous HCHO in the presence of Amberlyst A-21 in dichloromethane affords 2-nitro-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol (X), which is finally reduced with H2 over Ra-Ni to provide FTY-720.

1 Kalita, B.; Barua, N.C.; Bez, G; Bezbarua, M.; Synthesis of 2-nitro alcohols by regioselective ring opening of epoxides with MgSO4/NeOH/NaNO2 system: A short synthesis of immunosuppressive agent FTY-720. Synlett 2001, 9, 1411.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 29029 4-chlorobenzaldehyde 104-88-1 C7H5ClO 详情 详情
(II) 53249 iodo(octyl)zinc n/a C8H17IZn 详情 详情
(III) 53250 4-Octylbenzaldehyde 49763-66-8 C15H22O 详情 详情
(IV) 16524 bromo(vinyl)magnesium 1826-67-1 C2H3BrMg 详情 详情
(V) 53251 1-(4-octylphenyl)-2-propen-1-ol n/a C17H26O 详情 详情
(VI) 53252 (4-octylphenyl)(2-oxiranyl)methanol n/a C17H26O2 详情 详情
(VII) 53253 3-nitro-1-(4-octylphenyl)-1,2-propanediol n/a C17H27NO4 详情 详情
(VIII) 53254 1-[(E)-3-nitro-1-propenyl]-4-octylbenzene n/a C17H25NO2 详情 详情
(IX) 53255 1-(3-nitropropyl)-4-octylbenzene n/a C17H27NO2 详情 详情
(X) 53256 2-nitro-2-(4-octylphenethyl)-1,3-propanediol n/a C19H31NO4 详情 详情
Extended Information