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2. Alc to Sulf Ester
3. Alc to Tf
4. Ex (Tf2NPh)

Alcohol to Triflate

(Tf₂NPh)

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Examples:

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Example 1

To a solution of the SM (798 mg, 3.14 mmol) in DCM (7 mL) was added DMAP (38.3 mg, 0.314 mmol), TEA (1.31 mL, 9.41 mmol), and Tf2NPh (1.68 g, 4.71 mmol). The reaction mixture was stirred at RT for 90 min, after which time it was concentrated in vacuo. The resulting material was purified by Prep LC (50 g silica, 0-20% EtOAc/heptane) to provide the product as a yellow oil which crystallized upon standing. [1.17 g, 97%]

[Patent Reference: WO2015144799, page 250, (18.8 MB)]

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Example 2

A mixture of the SM (607 mg, 1.0 mmol), Tf2NPh (1.43 g, 4.0 mmol), and TEA (404 mg, 4.0 mmol) in THF (20 mL) was stirred for 70 C for 3 h. After cooling to RT, the mixture was poured into H2O (50 mL) and extracted with DCM (3 x 50 mL). The combined organics were dried, concentrated, and purified by silica gel chromatography (1:1 PE/EtOAc) to provide the product as a yellow solid. [600 mg, 82%] [WO2016011390, page 274]