Methanol → HCID 54148299, compound

HRID 1655997Notes

Reaction equation

HRID 1655997 reaction equation
[N:1]([C@H:4]([CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:5]1[O:10][CH:8]([OH:9])[C@H:7]([OH:11])[C@H:6]1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N+:2]=[N-:3].[CH3:29]O>C(Cl)Cl>[N:1]([C@H:4]([CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:5]1[O:10][CH:8]([O:9][CH3:29])[C@H:7]([OH:11])[C@H:6]1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 15598346HCID 15598346, compound

Product 1

HCID 54148299HCID 54148299, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-azido3,6-di-O-benzyl-5-deoxy-D-glucofuranose (10.23 g, 26.5 mmol) in methylene chloride (170 ml) was added methanol (11 ml) and borontrifluoroetherate (1.5 ml). The mixture was stirred 24 h at room temperature. The reaction mixture was successively washed with a saturated aqueous solution of sodium bicarbonate and then with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography on silica gel and elution with a 1:1 mixture of hexane and ethyl acetate afforded methyl 5-azido-3,6-di-O-benzyl-5-deoxy-D-glucofuranoside as a colorless oil (9.15 g, 85%).

Workup

  1. washThe reaction mixture was successively washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washFlash chromatography on silica gel and elution
  6. additionwith a 1:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-23ea5a47c9854a0391500a9a0c8883ed
Source dataset
uspto-grants-1993_10
Patent number
US05252587

Reaction notes

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