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【结 构 式】 
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【分子编号】16406 【品名】(3aR,5S,7aS)-5-azidohexahydro-1,3,2lambda(6)-benzodioxathiole-2,2-dione 【CA登记号】 |
【 分 子 式 】C6H9N3O4S 【 分 子 量 】219.22128 【元素组成】C 32.87% H 4.14% N 19.17% O 29.19% S 14.63% |
合成路线1
该中间体在本合成路线中的序号：(IXL)10) Albertini et al. reported a formal synthesis of epibatidine utilizing the enantiopure cyclohexanone (XXXVIII) as a convenient starting material which was easily available from D-(-)quinic acid (XXXVII). An important step in this synthesis was the regioselective intramolecular nucleophilic ring opening of the vicinal diol cyclic sulfate (XXXIX). When (XXXIX) was subjected to hydrogenation, the azido group was converted into an amino group and an internal displacement took place spontaneously to form the inner salt (XL). Three standard manipulations furnished the optically pure ketone (VIII), which had already been converted to epibatidine as described by Fletcher and coworkers.
| 【1】 Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G.P.; Zanirato, V.; Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(-)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine. Tetrahedron Lett 1997, 38, 4, 681-4. |
| 【2】 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IXL) | 16406 | (3aR,5S,7aS)-5-azidohexahydro-1,3,2lambda(6)-benzodioxathiole-2,2-dione | C6H9N3O4S | 详情 | 详情 | |
| (VIII) | 16374 | (1R,4S)-7-[(2,2-dimethylpropanoyl)oxy]-7-azabicyclo[2.2.1]heptan-2-one | C11H17NO3 | 详情 | 详情 | |
| (XXXVII) | 11524 | D-Quinic acid; D-(-)-Chinic acid; D-(-)-Quinic acid; (3R,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid | 77-95-2 | C7H12O6 | 详情 | 详情 |
| (XXXVIII) | 16405 | (3aR,7aS)-2,2-dimethyltetrahydro-1,3-benzodioxol-5(4H)-one | C9H14O3 | 详情 | 详情 | |
| (XL) | 16407 | (1R,2R,4S)-2-(sulfonatooxy)-7-azoniabicyclo[2.2.1]heptane | C6H11NO4S | 详情 | 详情 |