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【结 构 式】

【分子编号】60103

【品名】(4S)-4-benzyl-3-[4-(2-methyl-1,3-dithian-2-yl)butanoyl]-1,3-oxazolidin-2-one

【CA登记号】

【 分 子 式 】C19H25NO3S2

【 分 子 量 】379.54444

【元素组成】C 60.13% H 6.64% N 3.69% O 12.65% S 16.9%

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:(IV)

Chiral oxazolidinone intermediate (VI): The oxidation of the terminal double bond of the chiral acyl oxazolidinone (I) with O2 catalyzed by CuCl and PdCl2 in DMF/water gives the ketone (II), which is ketalized with propane-1,3-dithiol (III) and Ts-OH in AcOH to yield the thioketal (IV). Finally, the stereocontrolled acylation of (IV) with propionyl chloride (V) by means of LDA in THF affords the target oxazolidinone intermediate (VI)

1 Duan, M.S.; Paquette, L.A.; Highly diastereocontrolled synthesis of the C1-C25 domain of sanglifehrin A. Tetrahedron Lett 2000, 41, 20, 3789.
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) 60101 (4S)-4-benzyl-3-(5-hexenoyl)-1,3-oxazolidin-2-one C16H19NO3 详情 详情
(II) 60102 1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-1,5-hexanedione C16H19NO4 详情 详情
(III) 29729 1,3-propanedithiol; 3-sulfanylpropylhydrosulfide 109-80-8 C3H8S2 详情 详情
(IV) 60103 (4S)-4-benzyl-3-[4-(2-methyl-1,3-dithian-2-yl)butanoyl]-1,3-oxazolidin-2-one C19H25NO3S2 详情 详情
(V) 15967 propanoyl chloride; propionyl chloride 79-03-8 C3H5ClO 详情 详情
(VI) 60104 (2R)-1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-[2-(2-methyl-1,3-dithian-2-yl)ethyl]-1,3-pentanedione C22H29NO4S2 详情 详情
Extended Information