Triacetoxyperiodinane → HCID 59013442, compound

Participants

Reaction Steps

To a 0° 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 (1.0 mL) was added dropwise a solution of Dess-Martin reagent (43 mg, 0.1 mmol) in 0.5 mL of dry dichloromethane. The reaction mixture was stirred for 3.5 h at room temperature and quenched by addition of 2 mL of 1 M aqueous NaOH 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 1× with NaHSO3 (10 mL), 2× with NaHCO3 (10 mL), 3× with brine (10 mL) prior to drying over anhydrous Na2SO4. Concentration under reduced pressure and purification of the crude product by preparative TLC provided 36 mg of the pure product.

Provenance & Evidence