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【结 构 式】

【分子编号】60333

【品名】phenyl 1-[(trimethylsilyl)oxy]-1-propenyl ether; trimethyl{[1-(phenyloxy)-1-propenyl]oxy}silane

【CA登记号】

【 分 子 式 】C12H18O2Si

【 分 子 量 】222.35922

【元素组成】C 64.82% H 8.16% O 14.39% Si 12.63%

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)

Synthesis of intermediates: Iodinated pivalate (X): The condensation of 3-iodo-2-methyl-2-propenal (I) with the silylated enol ether (II) by means of Zr(O-tBu)4 and 3,3'-I2-BINOL in toluene gives the iodopentenoic acid (III), which is treated with Tips-Cl and imidazole to yield the silyl ether (IV). The reduction of (IV) by means of DIBAL in dichloromethane affords the 5-iodopenten-1-ol (V), which is oxidized by means of (COCl)2 in DMSO/dichloromethane to provide the aldehyde (VI). The Wittig condensation of (VI) with phosphorane (VII) in refluxing THF leads to the heptadienoic ester (VIII), which is reduced with DIBAL in dichloromethane giving the primary alcohol (IX). Finally this alcohol is esterified pivaloyl chloride and pyridine to affords the target iodinated pivalate (X).

1 Kobayashi, S.; Mori, K.; Wakabayashi, T.; Yasuda, S.; Hanada, K.; Convergent total synthesis of khafrefungin and its inhibitory activity of fungal sphigolipid syntheses. J Org Chem 2001, 66, 16, 5580.
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) 37952 (E)-3-iodo-2-methyl-2-propenal C4H5IO 详情 详情
(II) 60333 phenyl 1-[(trimethylsilyl)oxy]-1-propenyl ether; trimethyl{[1-(phenyloxy)-1-propenyl]oxy}silane C12H18O2Si 详情 详情
(III) 60334 phenyl 3-hydroxy-5-iodo-2,4-dimethyl-4-pentenoate C13H15IO3 详情 详情
(IV) 60335 phenyl 5-iodo-2,4-dimethyl-3-{[tris(1-methylethyl)silyl]oxy}-4-pentenoate C22H35IO3Si 详情 详情
(V) 60336 5-iodo-2,4-dimethyl-3-{[tris(1-methylethyl)silyl]oxy}-4-penten-1-ol C16H33IO2Si 详情 详情
(VI) 60337 5-iodo-2,4-dimethyl-3-{[tris(1-methylethyl)silyl]oxy}-4-pentenal C16H31IO2Si 详情 详情
(VII) 47172 propyl 2-(triphenylphosphoranylidene)propanoate C24H25O2P 详情 详情
(VIII) 60338 propyl 7-iodo-2,4,6-trimethyl-5-{[tris(1-methylethyl)silyl]oxy}-2,6-heptadienoate C22H41IO3Si 详情 详情
(IX) 60339 7-iodo-2,4,6-trimethyl-5-{[tris(1-methylethyl)silyl]oxy}-2,6-heptadien-1-ol C19H37IO2Si 详情 详情
(X) 60340 7-iodo-2,4,6-trimethyl-5-{[tris(1-methylethyl)silyl]oxy}-2,6-heptadienyl 2,2-dimethylpropanoate C24H45IO3Si 详情 详情
Extended Information