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【结 构 式】 
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【药物名称】Galamustine hydrochloride, G-6-M, C6-GalM, C6-GLM, C6-Galactose mustard 【化学名称】6-[Bis(2-chloroethyl)amino]-6-deoxy-D-galactopyranose hydrochloride 【CA登记号】107811-63-2, 105618-02-8 (free base) 【 分 子 式 】C10H20Cl3NO5 【 分 子 量 】340.6336 |
【开发单位】Georgetown University (Originator), Unimed (Originator), University of Pennsylvania (Originator) 【药理作用】Oncolytic Drugs, DNA-Damaging Drugs |
合成路线1
G-6-M is prepared as shown. All secondary hydroxyl groups of D-galactopyranose were protected by vicinal capping into bis(acetonides) yielding 1,2:3,4-di-O-isopropylidene-D-galactopyranose. This was tosylated at 6-CH2OH and alkylated at C-6 with diethanolamine. The hydroxyethyl groups of compound (II) were chlorinated and the acetonides deblocked with dilute aqueous acid to give 6-bis(2-chloroethyl)amino-6-deoxy-D-galactopyranose hydrochloride in an overall conversion of ca. 42%.
| 【1】 Plasee, T.F.; Galamustine Hydrochloride. Drugs Fut 1991, 16, 3, 205. |
| 【2】 Hammer, C.F.; Talebian, A.; Green, D.; McPherson, E.; Schein, P.S.; 6-bis-(2-Chloroethyl)amino-6-deoxy-D-galactopyranose hydrochloride: Synthesis, chemical characterization, murine P388 antitumor activity, and bone marrow toxicity. J Pharm Sci 1989, 78, 11, 918-21. |
| 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) | 11439 | [(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-di[1,3]dioxolo[4,5-b:4,5-d]pyran-5-yl]methyl 4-methylbenzenesulfonate | C19H26O8S | 详情 | 详情 | |
| (II) | 11440 | 2-[[[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-di[1,3]dioxolo[4,5-b:4,5-d]pyran-5-yl]methyl](2-hydroxyethyl)amino]-1-ethanol | C16H29NO7 | 详情 | 详情 | |
| (III) | 11441 | N-[[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-di[1,3]dioxolo[4,5-b:4,5-d]pyran-5-yl]methyl]-2-chloro-N-(2-chloroethyl)-1-ethanaminium | C16H28Cl2NO5 | 详情 | 详情 |