Dichloromethane → 2,5-Anhydro-6-azido-1,3,6-trideoxy-D-ribo-hexitol 4-Methanesulfonate

HRID 54827Notes

Reaction equation

HRID 54827 reaction equation
[N:1]([CH2:4][C@H:5]1[O:10][C@@H:8]([CH3:9])[CH2:7][C@@H:6]1[OH:11])=[N+:2]=[N-:3].CCN(C(C)C)C(C)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(Cl)Cl>C(OCC)(=O)C.CCCCCC>[CH3:21][S:22]([O:11][C@@H:6]1[C@@H:5]([CH2:4][N:1]=[N+:2]=[N-:3])[O:10][C@@H:8]([CH3:9])[CH2:7]1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 867503542,5-Anhydro-6-azido-1,3,6-trideoxy-D-ribo-hexitol

Product 1

HCID 867503562,5-Anhydro-6-azido-1,3,6-trideoxy-D-ribo-hexitol 4-MethanesulfonateYield 48.7%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound is prepared by the procedure of Example 277 using 0.192 g of product from Example 338, 0.316 g of Hunig's base, 0.280 g of methanesulfonyl chloride and 0.35 ml of methylene chloride to give after chromatography (Silica gel: 30% ethyl acetate/hexane) 0.140 g of the desired product.

Sources & evidence

ORD record
ord-62323ef1a777454e91fb92b70e40184f
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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