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

HRID 1422553

반응식

HRID 1422553 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 516892Sodium BicarbonateHCID 2734732[(2R,3S,4R)-4-acetyloxy-3-phenylmethoxy-3,4-dihydro-2H-pyran-2-yl]methyl acetateHCID 22326455Hydrobromide monohydrate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-263635c797c5441f9a11b6f5bc0ab991
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927506B2

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