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【结 构 式】

【分子编号】11087

【品名】1-methyl 3-[(1S)-1-undecyl-3-butenyl] (2S)-2-phenylpropanedioate

【CA登记号】

【 分 子 式 】C25H38O4

【 分 子 量 】402.57432

【元素组成】C 74.59% H 9.51% O 15.9%

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:(XXX)

The chiral aldehyde (XI) can also be obtained as follows: The reaction of dodecanal (XXV) with allylmagnesium bromide (XXVI) in THF gives 1-pentadecen-4-ol (XXVII) as a racemic mixture, which is esterified with 2(R)-acetoxy-2-phenylacetic acid (XXVIII) by means of dicyclohexylcarbodiimide (DCC) and dimethylaminopyridine (DMAP) to yield the diastereoisomeric mixture of esters (XXIX) and (XXX), which are separated by flash chromatography. The hydrolysis of (XXIX) and (XXX) with KOH in methanol affords the alcohols (XXXI) and (XXXII). The unwanted isomer (XXXII) can be isomerized to (XXXI) through the formation of the 4-nitrobenzoyl ester and hydrolysis with K2CO3. The benzylation of (XXXI) with benzyl bromide and KH in THF gives the benzyl ether (XXXIII), which is finally ozonolyzed to the desired aldehyde (XI) with O3 in methanol-dichloromethane.

1 Prous, J.; Mealy, N.; Castaner, J.; Orlistat. Drugs Fut 1994, 19, 11, 1003.
2 Tehim, A.; Chen, P.; Hanessian, S.; Total synthesis of (-)-tetrahydrolipstatin. J Org Chem 1993, 58, 27, 7768-81.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 11068 (3R)-3-(Benzyloxy)tetradecanal C21H34O2 详情 详情
(XXV) 11082 Lauraldehyde; Dodecanal 112-54-9 C12H24O 详情 详情
(XXVI) 10386 Allyl(bromo)magnesium 1730-25-2 C3H5BrMg 详情 详情
(XXVII) 11084 1-Pentadecen-4-ol C15H30O 详情 详情
(XXVIII) 11085 (2R)-3-Methoxy-3-oxo-2-phenylpropionic acid C10H10O4 详情 详情
(XXIX) 11086 1-methyl 3-[(1R)-1-undecyl-3-butenyl] (2S)-2-phenylpropanedioate C25H38O4 详情 详情
(XXX) 11087 1-methyl 3-[(1S)-1-undecyl-3-butenyl] (2S)-2-phenylpropanedioate C25H38O4 详情 详情
(XXXI) 11088 (4R)-1-Pentadecen-4-ol C15H30O 详情 详情
(XXXII) 11089 (4S)-1-Pentadecen-4-ol C15H30O 详情 详情
(XXXIII) 11090 (4R)-4-(Benzyloxy)-1-pentadecene; Benzyl (1R)-1-undecyl-3-butenyl ether C22H36O 详情 详情
Extended Information