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【结 构 式】 
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【分子编号】26519 【品名】(1R,2Z)-1-[(1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-(palmitoylamino)ethyl]-2-hexadecenyl benzoate 【CA登记号】 |
【 分 子 式 】C68H93NO11 【 分 子 量 】1100.48656 【元素组成】C 74.22% H 8.52% N 1.27% O 15.99% |
合成路线1
该中间体在本合成路线中的序号：(XV)Protection of the 4- and 6-hydroxyl groups of (XI) was achieved by conversion into the benzylidene acetal (XII) upon treatment with benzaldehyde and formic acid. The remaining 2- and 3-hydroxyl groups of (XII) were benzoylated with benzoyl chloride to afford the corresponding benzoate ester (XIII). After reduction of the azide group of (XIII) to amine (XIV) with H2S and pyridine, condensation with hexadecanoyl chloride produced the corresponding amide (XV). Deprotection of the acetal group of (XV) with TFA in CH2Cl2 gave diol (XVI), which was finally treated with SO3-Me3N complex, and then with NaHCO3 to form the title disulfate sodium salt.
| 【1】 Banville, J.; Martel, A.; Aruffo, A.A. (Bristol-Myers Squibb Co.); Sulfated beta-glycolipid derivs. as cell adhesion inhibitors. EP 0671406; JP 1995285985; US 5565433 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 | |
| 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 | |
| 16480 | Palmitoyl Chloride; hexadecanoyl chloride | 112-67-4 | C16H31ClO | 详情 | 详情 | |
| (XI) | 26515 | (1R,2Z)-1-((1S)-1-azido-2-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]ethyl)-2-hexadecenyl benzoate | C31H49N3O8 | 详情 | 详情 | |
| (XII) | 26516 | (1R,2Z)-1-((1S)-2-[[(2S,4aR,6S,7R,8R,8aR)-7,8-dihydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-azidoethyl)-2-hexadecenyl benzoate | C38H53N3O8 | 详情 | 详情 | |
| (XIII) | 26517 | (1R,2Z)-1-((1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-azidoethyl)-2-hexadecenyl benzoate | C52H61N3O10 | 详情 | 详情 | |
| (XIV) | 26518 | (1R,2Z)-1-((1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-aminoethyl)-2-hexadecenyl benzoate | C52H63NO10 | 详情 | 详情 | |
| (XV) | 26519 | (1R,2Z)-1-[(1S)-2-[[(2S,4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-1-(palmitoylamino)ethyl]-2-hexadecenyl benzoate | C68H93NO11 | 详情 | 详情 | |
| (XVI) | 26520 | (1R,2Z)-1-[(1S)-2-[[(2S,3R,4S,5S,6R)-3,4-bis(benzoyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy]-1-(palmitoylamino)ethyl]-2-hexadecenyl benzoate | C61H89NO11 | 详情 | 详情 |