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【结 构 式】 
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【分子编号】62657 【品名】{[(2S,3aS,4R,6aR)-2-phenyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl]methoxy}methyl methyl ether; (2S,3aS,4R,6aR)-4-[(methoxymethoxy)methyl]-2-phenyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 【CA登记号】 |
【 分 子 式 】C14H19NO4 【 分 子 量 】265.3092 【元素组成】C 63.38% H 7.22% N 5.28% O 24.12% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reduction of the Zinner's lactone (I) by means of LiAlH4 in THF gives the acetonide (II), which is selectively monoprotected by reaction with chloromethyl methyl ether to yield intermediate (III). The reaction of (III) with Ms-Cl in pyridine affords the dimesylate (IV), which is treated with NaN3 in hot DMF to provide the monoazido derivative (V). The reductocyclization of (V) by means of H2 over Pd/C in ethanol gives the chiral pyrrolidine derivative (VI), which is finally deprotected by treatment with HCl in hot methanol to yield the target (2R,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol (VII) intermediate.
| 【1】 Ikota, N.; Hanaki, A.; Improved synthesis of (2R,3S,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine derivatives. Chem Pharm Bull 1988, 36, 3, 1143. |
| 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) | 62652 | (2S,3aR,7R,7aS)-7-hydroxy-2-phenyltetrahydro-6H-[1,3]dioxolo[4,5-c]pyran-6-one | C12H12O5 | 详情 | 详情 | |
| (II) | 62653 | (1S)-1-[(2S,4S,5R)-5-(hydroxymethyl)-2-phenyl-1,3-dioxolan-4-yl]-1,2-ethanediol | C12H16O5 | 详情 | 详情 | |
| (III) | 62654 | (1S)-1-[(2S,4S,5R)-5-(hydroxymethyl)-2-phenyl-1,3-dioxolan-4-yl]-2-(methoxymethoxy)-1-ethanol | C14H20O6 | 详情 | 详情 | |
| (IV) | 62655 | ((2R,4R,5R)-5-{(1S)-2-(methoxymethoxy)-1-[(methylsulfonyl)oxy]ethyl}-2-phenyl-1,3-dioxolan-4-yl)methyl methanesulfonate | C16H24O10S2 | 详情 | 详情 | |
| (V) | 62656 | (1S)-1-[(2R,4R,5R)-5-(azidomethyl)-2-phenyl-1,3-dioxolan-4-yl]-2-(methoxymethoxy)ethyl methanesulfonate | C15H21N3O7S | 详情 | 详情 | |
| (VI) | 62657 | {[(2S,3aS,4R,6aR)-2-phenyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl]methoxy}methyl methyl ether; (2S,3aS,4R,6aR)-4-[(methoxymethoxy)methyl]-2-phenyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole | C14H19NO4 | 详情 | 详情 | |
| (VII) | 62658 | (2R,3S,4R)-2-(hydroxymethyl)-3,4-pyrrolidinediol | C5H11NO3 | 详情 | 详情 |