(2R,3S,4R)-2-(hydroxymethyl)-3,4-pyrrolidinediol -Drug Synthesis Database

【结构式】

【分子编号】62658

【品名】(2R,3S,4R)-2-(hydroxymethyl)-3,4-pyrrolidinediol

【CA登记号】

【分子式】C₅H₁₁NO₃

【分子量】133.14728

【元素组成】C 45.1% H 8.33% N 10.52% O 36.05%

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：(VII)

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.

参考文献中间体

合成目标

【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	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