Reaction #83091

ord-2aef14470f0c4c5986e96c5b4d60cd8a

Reaction equation

CC(C)(C)[Si](OC[C@H]1O[C@H](CN=[N+]=[N-])C[C@H]1O)(c1ccccc1)c1ccccc1
product
CC(C)(C)[Si](OC[C@H]1O[C@H](CN=[N+]=[N-])C[C@H]1O)(c1ccccc1)c1ccccc1
2,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol
CCN(CC)CC
triethylamine
CS(=O)(=O)Cl
methanesulfonylchloride
→
CC(C)(C)[Si](OC[C@H]1O[C@H](CN=[N+]=[N-])C[C@H]1OS(C)(=O)=O)(c1ccccc1)c1ccccc1
desired product
Yield 95.6%
CC(C)(C)[Si](OC[C@H]1O[C@H](CN=[N+]=[N-])C[C@H]1OS(C)(=O)=O)(c1ccccc1)c1ccccc1
2,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol 3-Methanesulfonate
Yield 95.6%

Reactants

CC(C)(C)[Si](OC[C@H]1O[C@H](CN=[N+]=[N-])C[C@H]1O)(c1ccccc1)c1ccccc1
product
CC(C)(C)[Si](OC[C@H]1O[C@H](CN=[N+]=[N-])C[C@H]1O)(c1ccccc1)c1ccccc1
2,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol
CCN(CC)CC
triethylamine
CS(=O)(=O)Cl
methanesulfonylchloride

Reagents

None

Solvents

ClCCl
methylene chloride
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionextracted with diethyl ether
  2. 2
    Concentrationconcentrated in vacuo
  3. 3
    Otherpurified by chromatography (silica gel: 0-50% ethyl acetate/hexane)

Procedure

To a 0° C. solution, under argon, of 3.78 g of product from Example 276 in 20 ml of dry methylene chloride is added, dropwise, 1.02 g of triethylamine and 1.16 g methanesulfonylchloride. The reaction mixture is stirred for 3 hours, diluted with water, extracted with diethyl ether, concentrated in vacuo, and purified by chromatography (silica gel: 0-50% ethyl acetate/hexane) to give 4.30 g of the desired product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05623081uspto-grants-1997_04