【结 构 式】 |
【分子编号】26265 【品名】(4R)-6-hydroxy-4-methylhexanal 【CA登记号】 |
【 分 子 式 】C7H14O2 【 分 子 量 】130.18696 【元素组成】C 64.58% H 10.84% O 24.58% |
合成路线1
该中间体在本合成路线中的序号:(II)The preparation of the precursor amino acids is shown in Schemes 1-4. Ozonolysis of (R)-citronellol (I), followed by Wittig reaction of the resulting aldehyde (II) with methylene triphenylphosphorane gave heptenol (III). Subsequent hydrogenation of (III) over Pd/C provided the saturated alcohol (IV), which was oxidized to the corresponding aldehyde (V) by treatment with Dess-Martin reagent. Asymmetric Strecker reaction in (V) utilizing (R)-phenylglycinol (VI) and trimethylsilyl cyanide afforded a diastereomeric mixture of aminonitriles (VII). After oxidative cleavage of (VII) with lead tetraacetate, the free (2S)-amine (VIII) was separated from its minor diastereomer by column chromatography. Acid hydrolysis of the nitrile group of (VIII) gave 5-propyl-L-leucine (IX), which was protected as the tert-butyl carbamate (X) with Boc2O.
【1】 Boger, D.L.; et al.; Total synthesis of HUN-7293. J Am Chem Soc 1999, 121, 26, 6197. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
27301 | methylene(triphenyl)phosphorane | C19H17P | 详情 | 详情 | ||
(A) | 18845 | Dess-Martin periodinane; 1,1,1-Triacetoxy-1,2-benziodoxol-3(1H)-one | 87413-09-0 | C13H13IO8 | 详情 | 详情 |
(I) | 26264 | (3R)-3,7-dimethyl-6-octen-1-ol | 1117-61-9 | C10H20O | 详情 | 详情 |
(II) | 26265 | (4R)-6-hydroxy-4-methylhexanal | C7H14O2 | 详情 | 详情 | |
(III) | 26266 | (3R)-3-methyl-6-hepten-1-ol | C8H16O | 详情 | 详情 | |
(IV) | 26267 | (3R)-3-methyl-1-heptanol | C8H18O | 详情 | 详情 | |
(V) | 26268 | (3R)-3-methylheptanal | C8H16O | 详情 | 详情 | |
(VI) | 14376 | (2R)-2-amino-2-phenyl-1-ethanol; (R)-(-)-2-phenylglycinol; (R)-2-amino-2-phenyl-1-ethanol | 56613-80-0 | C8H11NO | 详情 | 详情 |
(VII) | 26269 | (4R)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]-4-methyloctanenitrile | C17H26N2O | 详情 | 详情 | |
(VIII) | 26270 | (2S,4R)-2-amino-4-methyloctanenitrile | C9H18N2 | 详情 | 详情 | |
(IX) | 26271 | (2S,4R)-2-amino-4-methyloctanoic acid | C9H19NO2 | 详情 | 详情 | |
(X) | 26272 | (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-methyloctanoic acid | C14H27NO4 | 详情 | 详情 |