Sodium Thiosulfate → 2,6-Anhydro-5-azido-1-O-[tert-butyl(dimethyl)silyl]-4,5-dideoxy-L-erythro-hex-3-ulose

HRID 470705ノート

反応式

HRID 470705 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:23]([C@@H:26]1[CH2:31][C@H:30]([OH:32])[C@@H:29]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[O:28][CH2:27]1)=[N+:24]=[N-:25].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[N:23]([C@H:26]1[CH2:27][O:28][C@H:29]([CH2:33][O:34][Si:35]([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36])[C:30](=[O:32])[CH2:31]1)=[N+:24]=[N-:25]

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 866726081,5-Anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-ribo-hexitol

生成物 1

HCID 866726102,6-Anhydro-5-azido-1-O-[tert-butyl(dimethyl)silyl]-4,5-dideoxy-L-erythro-hex-3-ulose収率 76.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A Dess-Martin reagent (876 mg, 2.00 mmol) was added to a dichloromethane (10 ml) solution of 1,5-anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-ribo-hexitol (450 mg, 1.25 mmol) under ice cooling and the resulting mixture was stirred for 75 minutes. Aqueous sodium thiosulfate solution was added under ice cooling, then the resulting mixture was subjected to extraction with ether and the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=50:1→20:1 (v/v)] to give 272 mg (76%) of the title compound as a colorless oil.

後処理

  1. extractionthe resulting mixture was subjected to extraction with ether
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=50:1→20:1 (v/v)]

出典と根拠

ORDレコード
ord-7d4a8841c37049cb857eea5164869265
出典データセット
uspto-grants-2014_01
特許番号
US08629133B2

反応ノート

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