Sodium Azide → 3,4,6-Tri-O-Acetyl-2-Azido-2-Deoxy-alpha-D-Glucopyranosyl Bromide

HRID 430449

반응식

HRID 430449 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:8][C@H:9]1[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@@H:13]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:12][CH:11]=[CH:10]1)(=[O:7])[CH3:6].[Br-:24].[Li+]>C(#N)C.C(OCC)C>[C:5]([O:8][C@H:9]1[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@@H:13]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:12][C@H:11]([Br:24])[C@@H:10]1[N:1]=[N+:2]=[N-:3])(=[O:7])[CH3:6]

참가 물질

6

반응물 3

HCID 33557Sodium AzideHCID 82050Lithium BromideHCID 688303Tri-O-acetyl-D-glucal

생성물 1

HCID 107156093,4,6-Tri-O-Acetyl-2-Azido-2-Deoxy-alpha-D-Glucopyranosyl Bromide

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매3회

반응 조건

온도
-30 °C

실험 절차

A 1 L flask containing 400 mL of acetonitrile was charged with sodium azide (7.75 g, 119.2 mmol) and ceric ammonium nitrate (120.7 g, 219.4 mmol). The resulting suspension was cooled to −30° C. and a solution of tri-O-acetyl-D-glucal (20.75 g, 76.22 mmol) in 100 mL acetonitrile was added to it dropwise. The reaction mixture was stirred at −30° C. for 20 hours and then warmed to room temperature, taken up in 800 mL of diethyl ether and washed with water (3×250 mL). The organics were dried over magnesium sulfate, filtered, and the solvent removed in vacuo to yield an oil. This oil was placed in a 1 L flask containing 400 mL of acetonitrile and lithium bromide (33.53 g, 386.1 mmol) and stirred at room temperature for at least 4 hours. The solvent was removed in vacuo and the resulting residue was taken up in 400 mL of dichloromethane. The organic layer was washed with water (2×250 mL), dried over magnesium sulfate and filtered. The solvent was removed in vacuo to yield the title compound as a gold oil which was used directly as in Example 1.

후처리

  1. temperaturewarmed to room temperature
  2. washwashed with water (3×250 mL)
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto yield an oil
  7. customThis oil was placed in a 1 L flask
  8. stirringstirred at room temperature for at least 4 hours
  9. customThe solvent was removed in vacuo
  10. washThe organic layer was washed with water (2×250 mL)
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-3b676b87a8db431ba3fc6b7270b02e9a
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323176B1

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