Hydrogen Bromide → 2,3,4-Tri-O-Acetyl-6-Deoxy-alpha-D-Glucopyranosyl Bromide

HRID 433869

반응식

HRID 433869 반응식
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4].[BrH:12]>C(O)(=O)C.ClCCl>[C:3]([O:10][C@@H:9]1[C@@H:7]([O:8][C:5](=[O:6])[CH3:7])[C@H:5]([O:6][C:9](=[O:10])[CH3:11])[C@@H:3]([CH3:2])[O:4][C@@H:11]1[Br:12])(=[O:4])[CH3:2]

참가 물질

5

반응물 2

HCID 260Hydrogen BromideHCID 935796-Deoxyglucose

생성물 1

HCID 128982142,3,4-Tri-O-Acetyl-6-Deoxy-alpha-D-Glucopyranosyl Bromide수율 85.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

In a 10 mL round bottom flask containing 10 mL of glacial acetic acid was placed 6-deoxyglucose (332.3 mg) and the reaction was cooled to 0° C. Hydrobromic acid in glacial acetic acid (5 mL of a 30 wt. % solution) was added dropwise. The reaction was stirred for 4 hours. The reaction was diluted with 100 mL of dichloromethane and washed with 50 mL ice water and then 50 mL of cold saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate and filtered. The solvent was removed in vacuo to yield the title compound as a yellow solid (636.5 mg, 85.4%) and the product was used without further purification as in Example 1. MS (FAB) calculated for C12H17O7Br (M−Br) 273.1, found 273.1.

후처리

  1. washwashed with 50 mL ice water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-da861d3f276d4fffaed66d8205cdf948
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670324B2

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