(Diethylamino)sulfur trifluoride → HCID 59013482, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of (1S,3′R,4′S,5′R,6′R)-3′,4′,5′-tris(benzyloxy)-6′-(benzyloxymethyl)-5-chloro-6-(4-ethylbenzyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran]-3-ol (40 mg, 0.05 mmol) in dry dichloromethane (2.0 mL) was added dropwise a solution of DAST reagent (0.014 mL, 0.1 mmol, 95%) in 0.5 mL of dry dichloromethane. The reaction mixture was stirred for 2 h at −78° C. and quenched by addition of 1 mL of saturated aqueous NaHCO3 solution when TLC showed the reaction was complete. The organic layer was separated and the aqueous layer was extracted 2× with CH2Cl2 (10 mL). The combined organic layers were washed 2× with NaHCO3 (10 mL), 3× with brine (10 mL) prior to drying over anhydrous Na2SO4. Concentrated under reduced pressure and purification of the crude product by prepared TLC provided 35 mg of the pure product.

Provenance & Evidence