2-Methylbenzenesulfonic acid → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one

HRID 1261814ノート

反応式

HRID 1261814 の反応式
[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13](C(O)O)[O:12][C:11](=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH:30]([O:35][CH3:36])([O:33][CH3:34])OC.C([O-])(O)=O.[Na+]>ClCCl>[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH:30]([O:33][CH3:34])[O:35][CH3:36])[O:12][C:11](=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 69252-Methylbenzenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 44128178(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)-tetrahydropyran-2-one

生成物 1

HCID 68898127(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 1.0 g of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)-tetrahydropyran-2-one (V′) in 100 mL of dichloromethane, 50 mg of toluenesulfonic acid and 4.5 mL of trimethyl orthoformate are added. After 2 hours of stirring at 25° C., 0.2 g of NaHCO3 is added and dichloromethane is distilled off. The residue is flash chromatographed (MTBE/hexane 1/1) and the solvents are distilled off to get the title compound.

後処理

  1. distillationdichloromethane is distilled off
  2. customchromatographed (MTBE/hexane 1/1)
  3. distillationthe solvents are distilled off

出典と根拠

ORDレコード
ord-bee5a76418024f21ab86773691b6ce96
出典データセット
uspto-grants-2013_06
特許番号
US08471045B2

反応ノート

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