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【结 构 式】 
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【分子编号】14549 【品名】(4S)-4-[(1S)-1-azido-2-phenylethyl]-1,3,2lambda(6)-dioxathiolane-2,2-dione 【CA登记号】 |
【 分 子 式 】C10H11N3O4S 【 分 子 量 】269.28116 【元素组成】C 44.6% H 4.12% N 15.6% O 23.77% S 11.91% |
合成路线1
该中间体在本合成路线中的序号：(XXXIV)4) The selective esterification of 3(S)-azido-4-phenylbutane-1,2(S)-diol (XXIX) with 2,4,6-triiosopropylbenzenesulfonyl chloride (XXX) gives the sulfonate ester (XXXI), which by treatment with KOH is converted to the azido epoxide (XXXII). The condensation of (XXXII) with decahydroisoquinoline (XI) affords the azido condensation product (XXXIII), which is finally hydrogenated with H2 over Pd/C to the amino condensation product (XIII), already obtained in scheme 16810301a. 5) The reaction of (XXIX) with SOCl2 and RuCl3 gives the dioxathiole dioxide (XXXIV), which is condensed with decahydroisoquinoline (XI) to afford the azido condensation product (XXXIII), already obtained.
| 【1】 Parkes, K.E.B.; Bushnell, D.J.; Crackett, P.H.; et al.; Studies toward the large-scale synthesis of the HIV proteinase inhibitor Ro 31-8959. J Org Chem 1994, 59, 13, 3656. |
| 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) | 13955 | (3S,4aS,8aS)-N-(tert-Butyl)decahydro-3-isoquinolinecarboxamide | C14H26N2O | 详情 | 详情 | |
| (XIII) | 14528 | (3S,4aS,8aS)-2-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(tert-butyl)decahydro-3-isoquinolinecarboxamide | C24H39N3O2 | 详情 | 详情 | |
| (XXIX) | 14544 | (2S,3S)-3-azido-4-phenyl-1,2-butanediol | C10H13N3O2 | 详情 | 详情 | |
| (XXX) | 14545 | 2,4,6-triisopropylbenzenesulfonyl chloride | 6553-96-4 | C15H23ClO2S | 详情 | 详情 |
| (XXXI) | 14546 | (2S,3S)-3-azido-2-hydroxy-4-phenylbutyl 2,4,6-triisopropylbenzenesulfonate | C25H35N3O4S | 详情 | 详情 | |
| (XXXII) | 14547 | (1S)-1-[(2S)oxiranyl]-2-phenylethyl azide; (2S)-2-[(1S)-1-azido-2-phenylethyl]oxirane | C10H11N3O | 详情 | 详情 | |
| (XXXIII) | 14548 | (3S,4aS,8aS)-2-[(2R,3S)-3-(1-azanylhydrazino)-2-hydroxy-4-phenylbutyl]-N-(tert-butyl)decahydro-3-isoquinolinecarboxamide | C24H41N5O2 | 详情 | 详情 | |
| (XXXIV) | 14549 | (4S)-4-[(1S)-1-azido-2-phenylethyl]-1,3,2lambda(6)-dioxathiolane-2,2-dione | C10H11N3O4S | 详情 | 详情 |