Triethylamine → 2,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol 3-Methanesulfonate

HRID 1290428Notes

Reaction equation

HRID 1290428 reaction equation
[N:1]([CH2:4][C@H:5]1[O:28][C@H:8]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]([OH:29])[CH2:6]1)=[N+:2]=[N-:3].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl.O>[CH3:37][S:38]([O:29][C@@H:7]1[CH2:6][C@@H:5]([CH2:4][N:1]=[N+:2]=[N-:3])[O:28][C@@H:8]1[CH2:9][O:10][Si:11]([C:24]([CH3:25])([CH3:26])[CH3:27])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:40])=[O:39]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 867503512,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol

Product 1

HCID 867503522,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol 3-MethanesulfonateYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-c1d4174750304e73892329df08be8527
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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