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【结 构 式】 
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【药物名称】NSC-322328, GYKI-17230 【化学名称】1,6-Di-O-methylsulfonyl-3,4-di-O-methyl-D-mannitol 【CA登记号】71240-74-9 【 分 子 式 】C10H22O10S2 【 分 子 量 】366.40884 |
【开发单位】Chinoin (Originator) 【药理作用】Oncolytic Drugs |
合成路线1
Condensation of D-mannitol (I) with acetone by means of zinc chloride gives 1,2,5,6-di-O isopropylidene-D-mannitol (II), which on treatment with dimethyl sulfate in DMSO in the presence of NaOH gives the 3,4-di-O-methyl derivative (III). Removal of the isopropylidene groups of (III) by HCl in boiling ethanol gives 3,4-di-O-methyl-o-mannitol (IV), a solution of which in pyridine is treated with methanesulfonyl chloride and subsequently with acetic anhydride to give 1,6-di-O-methylsulfonyl-2,5-di-O-acetyl-3,4-di-O-methyl-D-mannitol (V), deacetylation of which is carried out in methanol by means of hydrochloric acid.
| 【1】 Kuszmann, J.; Csanyi, E.; Kiraly, E.; GYKI-17230. Drugs Fut 1987, 12, 1, 18. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 23199 | 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether | 67-64-1 | C3H6O | 详情 | 详情 | |
| (I) | 23078 | 1,2,3,4,5,6-hexanehexol | C6H14O6 | 详情 | 详情 | |
| (II) | 23079 | 1,2-bis(2,2-dimethyl-1,3-dioxolan-4-yl)-1,2-ethanediol | C12H22O6 | 详情 | 详情 | |
| (III) | 23080 | 1,2-bis(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methoxyethyl methyl ether; 4-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-1,2-dimethoxyethyl]-2,2-dimethyl-1,3-dioxolane | C14H26O6 | 详情 | 详情 | |
| (IV) | 23081 | 3,4-dimethoxy-1,2,5,6-hexanetetrol | C8H18O6 | 详情 | 详情 | |
| (V) | 23082 | 4-(acetoxy)-2,3-dimethoxy-5-[(methylsulfonyl)oxy]-1-[[(methylsulfonyl)oxy]methyl]pentyl acetate | C14H26O12S2 | 详情 | 详情 |