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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information