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【结 构 式】 
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【分子编号】24264 【品名】(1S,5S,6S,7R,8S)-6,7,8-trihydroxy-1-(hydroxymethyl)-4-methyl-2-oxa-4-azabicyclo[3.3.1]nonan-3-one 【CA登记号】 |
【 分 子 式 】C9H15NO6 【 分 子 量 】233.22124 【元素组成】C 46.35% H 6.48% N 6.01% O 41.16% |
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：(V)The acylation of valienamine (I) with benzyloxycarbonyl chloride (II) by means of NaHCO3 in ethyl acetate gives the corresponding N-benzyloxycarbonyl derivative (III), which by reaction with Br2 in water is converted to the cyclic carbamate (IV). Elimination of bromine from (IV) with NaBH4 in water affords the new cyclic carbamate (V), which by hydrolysis with Ba(OH)2 in refluxing water is converted to valiolamine (VI). Finally, this compound is reductocondensed with 1,3-dihydroxyacetone (VII) and sodium cyanoborohydride in DMF 2N HCl.
| 【1】 Horii, S.; et al.; Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents. J Med Chem 1986, 29, 6, 1038. |
| 【2】 Horii, S.; Kameda, Y.; Fukase, H. (Takeda Chemical Industries, Ltd.); N-substituted pseudo-aminosugars, their production and use. EP 0056194; US 4701559; US 4777294; US 4803303 . |
| 【3】 Prous, J.; Castaner, J.; AO-128. Drugs Fut 1986, 11, 9, 729. |
| 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) | 24260 | (1S,2S,3R,6S)-4-(hydroxymethyl)-6-(methylamino)-4-cyclohexene-1,2,3-triol | C8H15NO4 | 详情 | 详情 | |
| (II) | 24261 | 1-[2-(chlorooxy)-2-oxoethyl]benzene | C8H7ClO2 | 详情 | 详情 | |
| (III) | 24262 | (1S,2S,3R,6S)-4-(hydroxymethyl)-6-[methyl[(2-phenylacetyl)oxy]amino]-4-cyclohexene-1,2,3-triol | C16H21NO6 | 详情 | 详情 | |
| (IV) | 24263 | (1S,5R,6S,7R,8S,9S)-9-bromo-6,7,8-trihydroxy-1-(hydroxymethyl)-4-methyl-2-oxa-4-azabicyclo[3.3.1]nonan-3-one | C9H14BrNO6 | 详情 | 详情 | |
| (V) | 24264 | (1S,5S,6S,7R,8S)-6,7,8-trihydroxy-1-(hydroxymethyl)-4-methyl-2-oxa-4-azabicyclo[3.3.1]nonan-3-one | C9H15NO6 | 详情 | 详情 | |
| (VI) | 24265 | (1S,2S,3R,4S,5S)-1-(hydroxymethyl)-5-(methylamino)-1,2,3,4-cyclohexanetetrol | C8H17NO5 | 详情 | 详情 | |
| (VII) | 14575 | Dihydroxyacetone; 1,3-dihydroxyacetone | 96-26-4 | C3H6O3 | 详情 | 详情 |
Extended Information