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【结 构 式】

【分子编号】37794

【品名】(4S)-4-benzyl-3-[(2R)-2-[(benzyloxy)methyl]pentanoyl]-1,3-oxazolidin-2-one

【CA登记号】

【 分 子 式 】C23H27NO4

【 分 子 量 】381.47172

【元素组成】C 72.42% H 7.13% N 3.67% O 16.78%

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:(V)

The intermediate (R)-formyl amide (IX) was synthesized as follows. Acylation of the lithium anion of (S)-4-benzyl-2-oxazolidinone (I) with valeryl chloride (II) provided acyl oxazolidinone (III). Subsequent diastereoselective benzyloxymethylation of (III) with chloride (IV) and TiCl4 gave benzyl ether (V). Hydrolysis of (V) with lithium peroxide, followed by coupling of the resulting carboxylic acid (VI) with diethylamine in the presence of TBTU yielded diethylamide (VII). Hydrogenolysis of the benzyl group of (VII) using Pearlman's catalyst afforded alcohol (VIII), which was oxidized to aldehyde (IX) by means of Dess-Martin periodinane or NaOCl in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy radical (TEMPO) to give (IX).

1 Soucy, F.; et al.; A novel and efficient synthesis of a highly active analogue clasto-lactacystin beta-lactone. J Am Chem Soc 1999, 121, 43, 9967.
2 Plamondon, L.; Soucy, F.; Behnke, M.; Roush, W.; Synthesis of clasto-lactacystin beta-lactone and analogs thereof. WO 9909006 .
3 Plamondon, L.; Adams, J.; Elliot, P. (ProScript, Inc.); Proteasome inhibitors, ubiquitin pathway inhibitors or agents that interfere with the activation of NF-kappaB via the ubiquitin proteasome pathway to treat inflammatory and autoimmune diseases. WO 9915183 .
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) 14694 (S)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-1,3-oxazolan-2-one; (S)-(-)-4-Benzyl-2-oxazolidinone 90719-32-7 C10H11NO2 详情 详情
(II) 15116 pentanoyl chloride; valeryl chloride 638-29-9 C5H9ClO 详情 详情
(III) 29431 (4S)-4-benzyl-3-pentanoyl-1,3-oxazolidin-2-one C15H19NO3 详情 详情
(IV) 14560 Benzyl chloromethyl ether; 1-[(chloromethoxy)methyl]benzene 3587-60-8 C8H9ClO 详情 详情
(V) 37794 (4S)-4-benzyl-3-[(2R)-2-[(benzyloxy)methyl]pentanoyl]-1,3-oxazolidin-2-one C23H27NO4 详情 详情
(VI) 37795 (2R)-2-[(benzyloxy)methyl]pentanoic acid C13H18O3 详情 详情
(VII) 37796 (2R)-2-[(benzyloxy)methyl]-N,N-diethylpentanamide C17H27NO2 详情 详情
(VIII) 37797 (2R)-N,N-diethyl-2-(hydroxymethyl)pentanamide C10H21NO2 详情 详情
(IX) 37798 (2R)-N,N-diethyl-2-formylpentanamide C10H19NO2 详情 详情
Extended Information