[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][OH:8])[CH2:2]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:16][S:17]([O:8][CH2:7][CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:19])=[O:18]2-(Tetrahydro-3-furanyl)ethanol (230 mg) was dissolved in dry DCM (5 mL) and triethylamine (0.552 mL) was added. The stirred solution was cooled (ice bath) under nitrogen and methanesulphonyl chloride (0.199 mL) was added dropwise over 5 mins. The mixture was allowed to warm slowly to room temperature as the ice bath melted and was left for 16 h. The mixture was shaken with saturated sodium bicarbonate solution and the aqueous layer was extracted with DCM (×2). The combined organics were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound (364 mg).
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