Dichloromethane → 1,5-Anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-ribo-hexitol

HRID 470702Notes

Reaction equation

HRID 470702 reaction equation
ClCCl.[C:4]([Si:8]([CH3:11])([CH3:10])Cl)([CH3:7])([CH3:6])[CH3:5].[N:12]([C@@H:15]1[CH2:20][C@H:19]([OH:21])[C@@H:18]([CH2:22][OH:23])[O:17][CH2:16]1)=[N+:13]=[N-:14].C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:12]([C@@H:15]1[CH2:20][C@H:19]([OH:21])[C@@H:18]([CH2:22][O:23][Si:8]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:11])[CH3:10])[O:17][CH2:16]1)=[N+:13]=[N-:14]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 866726091,5-Anhydro-2-azido-2,3-dideoxy-D-glucitol

Product 1

HCID 866726081,5-Anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-ribo-hexitolYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A dichloromethane (4 ml) solution of tert-butyldimethylchlorosilane (381 mg, 2.54 mmol) was added to a dichloromethane (10 ml) solution of 1,5-anhydro-2-azido-2,3-dideoxy-D-ribo-hexitol (440 mg, 2.54 mmol) and triethylamine (0.46 ml, 3.30 mmol) under ice cooling. After stirring at room temperature for 50 hours, the reaction mixture was diluted with chloroform and the organic layer was washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=10:1→4:1 (v/v)] to give 650 mg (89%) of the title compound as a colorless oil.

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=10:1→4:1 (v/v)]

Sources & evidence

ORD record
ord-fd155648853541b3aec9b0c2bda80fd3
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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