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【结 构 式】 
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【药物名称】D-threo-PDPP 【化学名称】(R,R)-N-[2-Hydroxy-2-phenyl-1-(1-pyrrolidinylmethyl)ethyl]decanamide 【CA登记号】193545-89-0 【 分 子 式 】C23H38N2O2 【 分 子 量 】374.57151 |
【开发单位】Seikagaku (Originator) 【药理作用】Gaucher's Disease, Agents for, METABOLIC DRUGS, ONCOLYTIC DRUGS, Therapy of Inborn Errors of Metabolism, Ceramide Glucosyltransferase Inhibitors |
合成路线1
(1R,2R)-2-Benzyloxycarbonylamino-1-phenyl-1,3-propanediol (I) was converted to mesylate (II) upon treatment with methanesulfonyl chloride in pyridine. Reaction of this mesylate with pyrrolidine (III) provided pyrrolidino compound (IV). The N-benzyloxycarbonyl group of (IV) was then eliminated by hydrogenolysis over Pd/C to yield the vicinal hydroxyamine (V), which was finally condensed with decanoyl chloride (VI) to furnish the target decanoyl amide.
| 【1】 Oyamada, H.; Inokuchi, J.; Jinbo, M. (Seikagaku Corp.); Amino alcohol deriv. and method for preparing the . EP 0782992 . |
| 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) | 22793 | phenyl (1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-phenylethylcarbamate | C16H17NO4 | 详情 | 详情 | |
| (II) | 22794 | (2R,3R)-3-hydroxy-2-[(phenoxycarbonyl)amino]-3-phenylpropyl methanesulfonate | C17H19NO6S | 详情 | 详情 | |
| (III) | 11376 | Pyrrolidine | 123-75-1 | C4H9N | 详情 | 详情 |
| (IV) | 22796 | phenyl (1R,2R)-2-hydroxy-2-phenyl-1-(1-pyrrolidinylmethyl)ethylcarbamate | C20H24N2O3 | 详情 | 详情 | |
| (V) | 22797 | (1R,2R)-2-amino-1-phenyl-3-(1-pyrrolidinyl)-1-propanol | C13H20N2O | 详情 | 详情 | |
| (VI) | 22798 | 1-chloro-2-undecanone | C11H21ClO | 详情 | 详情 |