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【结 构 式】 
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【分子编号】16479 【品名】2,3-dihydroxypropyl nicotinate 【CA登记号】 |
【 分 子 式 】C9H11NO4 【 分 子 量 】197.19068 【元素组成】C 54.82% H 5.62% N 7.1% O 32.45% |
合成路线1
该中间体在本合成路线中的序号：(IV)The compound S 16961-1 was synthesized in three steps from solketal (I) by acylation with nicotinoyl chloride (II), deprotection of the isopropylidene ketal (III) by heating in dilute aqueous acetic acid and acylation of this key intermediate (IV) with a slight excess of palmitoyl chloride (V) in the presence of triethylamine and 4-dimethylaminopyridine (DMAP) as catalyst. The enantiomers of S 16961-1 were obtained independently in one step from the commercially available (d)- and (l)-1,2-dipalmitoyl glycerols by acylation with nicotinoyl chloride in the presence of triethylamine. The enantiomers were found equiactive and therefore were not pursued individually.
| 【1】 Brown, G.; Albers, J.J.; Fisher, L.D.; Schaeffer, S.; Lin, J.; Kaplan, C.; Zhao, X.; Bisson, B.; Fitzpatrick, V.; Dodge, H.; Regression of coronary artery disease as a result of intensive lipid lowering therapy in men with high level of apolipoprotein B. New Engl J Med 1990, 323, 19, 1289-98. |
| 【2】 Cordi, A.A.; Duhault, J.; Laudignon, N.; Castagne, I.; S 16961-1. Drugs Fut 1996, 21, 5, 490. |
| 【3】 Cordi, A.; Lacoste, J.-M.; Duhault, J.; Espinal, J.; Boulanger, M. (ADIR et Cie.); Diacylglycerol nicotinates. EP 0574312; JP 1994056786; US 5385920 . |
| 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) | 16476 | 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane; (2,2-dimethyl-1,3-dioxolan-4-yl)methanol; 2,3-o-Isopropylideneglycerol | 100-79-8 | C6H12O3 | 详情 | 详情 |
| (II) | 10753 | Nicotinoyl chloride | C6H4ClNO | 详情 | 详情 | |
| (III) | 16478 | (2,2-dimethyl-1,3-dioxolan-4-yl)methyl nicotinate | C12H15NO4 | 详情 | 详情 | |
| (IV) | 16479 | 2,3-dihydroxypropyl nicotinate | C9H11NO4 | 详情 | 详情 | |
| (V) | 16480 | Palmitoyl Chloride; hexadecanoyl chloride | 112-67-4 | C16H31ClO | 详情 | 详情 |