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【结 构 式】

【分子编号】43784

【品名】diisopropyl (2S,3R)-2-hydroxy-3-(2-methyl-2-propenyl)butanedioate

【CA登记号】

【 分 子 式 】C14H24O5

【 分 子 量 】272.34156

【元素组成】C 61.74% H 8.88% O 29.37%

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:(III)

Treatment of butanedioate derivative (I) with methallyl iodide (II) and LDA in THF affords alkene (III), which is then reduced by hydrogenation over Pd/C and subjected to saponification by means of KOH in dioxane to yield succinic acid (IV). Protection of (IV) with 2,2-dimethoxypropane (V) and p-TsOH in DMF provides derivative (VI), which is then coupled with pentafluorophenol (VII) by using EDC in CH2Cl2 to furnish activated ester (VIII). Displacement of the pentafluorophenol moiety of (VIII) by treatment with L-tert-leucine methylamide (IX) in DMF gives methylamide derivative (X), which is deprotected with THF and HCl and condensed with O-benzylhydroxylamine (XI) by means of EDC to afford derivative (XII). Finally, (XII) is debenzylated by hydrogenation over Pd/C in EtOH to give the target compound.

1 Davenport, R.J.; Watson, R.J.; An improved synthesis of the broad spectrum matrix metalloprotease inhibitor marimastat. Tetrahedron Lett 2000, 41, 41, 7983.
2 Dickens, J.P.; Crimmin, M.J.; Beckett, R.P. (British Biotech plc); Natural amino acid derivs. as metalloproteinase inhibitors. EP 0651738; EP 0651739; GB 2268933; GB 2268934; JP 1995509460; JP 1998204081; WO 9402446; WO 9402447 .
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) 43782 diisopropyl (2S)-2-hydroxybutanedioate C10H18O5 详情 详情
(II) 43783 3-iodo-2-methyl-1-propene C4H7I 详情 详情
(III) 43784 diisopropyl (2S,3R)-2-hydroxy-3-(2-methyl-2-propenyl)butanedioate C14H24O5 详情 详情
(IV) 43785 (2S,3R)-2-hydroxy-3-isobutylbutanedioic acid C8H14O5 详情 详情
(V) 10722 1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane 77-76-9 C5H12O2 详情 详情
(VI) 43786 (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoic acid C11H18O5 详情 详情
(VII) 22662 2,3,4,5,6-pentafluorophenol 771-61-9 C6HF5O 详情 详情
(VIII) 43787 2,3,4,5,6-pentafluorophenyl (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate C17H17F5O5 详情 详情
(IX) 18843 (2S)-2-amino-N,3,3-trimethylbutanamide 89226-12-0 C7H16N2O 详情 详情
(X) 43788 (2R)-N-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanamide C18H32N2O5 详情 详情
(XI) 14640 O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene 622-33-3 C7H9NO 详情 详情
(XII) 43789 (2S,3R)-N(1)-(benzyloxy)-N(4)-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-2-hydroxy-3-isobutylbutanediamide C22H35N3O5 详情 详情
Extended Information