Imidazole → (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester

HRID 1025255ノート

反応式

HRID 1025255 の反応式
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([C@H:8]([OH:19])[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][CH:6]=C.C[SiH]([O:24]C(C)(C)C)C.[C:29]([Si:33]([CH3:36])([CH3:35])Cl)([CH3:32])([CH3:31])[CH3:30].N1C=CN=C1.N1C(C)=CC=CC=1C>CN(C=O)C.CC(O)(C)C.O1CCOCC1.O.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:5][CH:6]=[O:24])[C@H:8]([O:19][Si:33]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:36])[CH3:35])[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

10

反応物 5

HCID 795ImidazoleHCID 79372,6-LutidineHCID 28928tert-Butyldimethylsilyl chlorideHCID 67234162(R)-2-((R)-3-benzyloxy-1-hydroxypropyl)pent-4-enoic acid methyl esterHCID 71403863(Tert-butoxy)dimethylsilane

生成物 1

HCID 86654300(2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester収率 88%

試薬・触媒・溶媒 4

HCID 30318Osmium Tetroxide触媒HCID 6228Dimethylformamide溶媒HCID 6386tert-Butanol溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
25 °C

実験手順

The compound obtained in example 3e was protected as the tert-butyl dimethyl silyl ether by treatment with tert-butyldimethylchlorosilane and imidazole in DMF. This compound was treated with 2,6-lutidine and OsO4 2.5% in 2-methyl-2-propanol, followed by NalO4 in 1,4-dioxane—water (3:1) at room temperature. The reaction was stirred at 25° C. for 2 hrs, quenched, and the product purified by chromatography to provide (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester in 88% yield.

後処理

  1. customquenched
  2. customthe product purified by chromatography

出典と根拠

ORDレコード
ord-ad6901e5134345ce9dd889a19c07290e
出典データセット
uspto-grants-2014_05
特許番号
US08728515B2

反応ノート

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