Sodium ethanethiolate → 5-chloro-4-(4-ethylbenzyl)-2-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(2-methylallyl)tetrahydro-2H-pyran-2-yl)phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of sodium ethanethiolate (151 mg, 1.79 mmol) and 24 (150 mg, 0.179 mmol) in DMF (3 mL) was flushed with argon and heated at 90° C. for 3 h. The reaction mixture was cooled to 0° C. A mixture of acetic acid and water (1:1, 2 mL) was added. The resulting mixture was stirred for 10 min and then concentrated to dryness. The residue was partitioned between water and dichloromethane. The organic layer was separated, dried (Na2SO4), and evaporated. The residue was purified by preparatory TLC eluting with 10% EtOAc in petroleum ether to give 25 (135 mg, 92%). LC/MS m/z 846 (M+Na).

Provenance & Evidence