Water → 4-O-benzyl-3,6-di-O-acetyl-D-glucose

HRID 1422553

反応式

HRID 1422553 の反応式
[OH2:1].Br.[CH2:3]([O:10][C@@H:11]1[C@@H:16]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[O:15][CH:14]=[CH:13][C@H:12]1[O:22][C:23](=[O:25])[CH3:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH2:26].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:3]([O:10][C@H:11]([C@@H:16]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[OH:15])[C@H:12]([O:22][C:23](=[O:25])[CH3:24])[C@@H:13]([OH:26])[CH:14]=[O:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 516892Sodium BicarbonateHCID 2734732[(2R,3S,4R)-4-acetyloxy-3-phenylmethoxy-3,4-dihydro-2H-pyran-2-yl]methyl acetateHCID 22326455Hydrobromide monohydrate

生成物 1

HCID 866548394-O-benzyl-3,6-di-O-acetyl-D-glucose

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

48% Hydrobromic acid water solution (0.5 mL) was added to a mixture of 4-O-benzyl-3,6-di-O-acetyl-D-glucal (5 mmol) in tetrahydrofuran (50 mL), and obtained solution was stirred in room temperature. After reaction was completed (TLC) the reaction mixture was poured into the 10% water solution of sodium bicarbonate (125 mL), and water solution was extracted with ethyl acetate (3×30 mL). Combined organic extracts were washed with water and dried over sodium sulfate. Drying agent and solvents were removed and product was purified by column chromatography (SilicaGel 60 Merck), using hexanes:ethyl acetate as eluents.

後処理

  1. customobtained solution
  2. customAfter reaction
  3. extractionwas extracted with ethyl acetate (3×30 mL)
  4. washCombined organic extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. customDrying agent and solvents
  7. customwere removed
  8. customproduct was purified by column chromatography (SilicaGel 60 Merck)

出典と根拠

ORDレコード
ord-263635c797c5441f9a11b6f5bc0ab991
出典データセット
uspto-grants-2015_01
特許番号
US08927506B2

関連ノート

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