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【结 构 式】

【分子编号】54628

【品名】benzyl (1S,2S)-1-(hydroxymethyl)-2-methylbutyl(methyl)carbamate

【CA登记号】

【 分 子 式 】C15H23NO3

【 分 子 量 】265.35256

【元素组成】C 67.9% H 8.74% N 5.28% O 18.09%

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:(III)

The methylation of N-(benzyloxycarbonyl)-L-isoleucine (I) with Me-I and NaH in THF gives the N-methyl derivative (II), which is reduced with BH3 in THF to yield the isoleucinol (III). The oxidation of (III) with SO3/pyridine in DMSO affords the isoleucinal (IV), which is condensed with tert-butyl acetate (V) by means of BuLi and THF to afford the chiral beta-hydroxyheptanoate (VI). Finally, this compound is O-methylated by means of diazomethane and BF3 in ethyl ether/dichloromethane and N-deprotected by hydrogenation with H2 over Pd/C in ethyl acetate/methanol to provide the desired intermediate, the chiral tert-butyl heptanoate (VII).

1 Pettit, G.R.; Singh, S.B.; Williams, M.D.; Herald, D.L.; Hogan, F.; Burkett, D.D.; Clewlow, P.J.; The absolute configuration and synthesis of natural (-)-Dolastatin 10. J Am Chem Soc 1989, 111, Suppl. 3, 5463.
2 Pettit, G.R.; Srirangam, J.K.; Singh, S.B.; Williams, M.D.; Herald, D.L.; Barkóczy, J.; Kantoci, D.; Hogan, F.; Dolastatins 24. Synthesis of (-)-dolastatin 10. X-Ray molecular structure of N,N-dimethylvalyl-valyl-dolaisoleucine tert-butyl ester. J Chem Soc Perkins Trans I 1996, 8, Suppl. 3, 859-63.
3 Pettit, G.R.; Singh, S.B. (Arizona State University); Synthesis of dolastatin 10. US 4978744 .
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) 23508 (2S,3S)-2-[[(benzyloxy)carbonyl]amino]-3-methylpentanoic acid 3160-59-6 C14H19NO4 详情 详情
(II) 54627 (2S,3S)-2-[[(benzyloxy)carbonyl](methyl)amino]-3-methylpentanoic acid C15H21NO4 详情 详情
(III) 54628 benzyl (1S,2S)-1-(hydroxymethyl)-2-methylbutyl(methyl)carbamate C15H23NO3 详情 详情
(IV) 54629 benzyl (1S,2S)-1-formyl-2-methylbutyl(methyl)carbamate C15H21NO3 详情 详情
(V) 13597 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride 3282-30-2 C5H9ClO 详情 详情
(VI) 54630 tert-butyl (3R,4S,5S)-4-[[(benzyloxy)carbonyl](methyl)amino]-3-hydroxy-5-methylheptanoate C21H33NO5 详情 详情
(VII) 23514 tert-butyl (3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)heptanoate C14H29NO3 详情 详情
Extended Information