Benzyl Alcohol → HCID 23392918, compound

Participants

Reaction Steps

To a solution of benzyl mannopyranoside 18 (500 mg, 1.9 mmol; Synthesized via reflux in dry 1.0 Molar benzyl alcohol with 0.01 equivalents CSA, the reaction mixture is passed through a SiO2 column; benzyl alcohol comes out first using EtOAc:Hexane 1:5, then benzyl pyranoside is separated from the furanose byproduct with EtOAc as eluent) in dry pyridine (5 mL) at 0° C. was added tosyl chloride (381 mg, 2 mmol; Aldrich) dissolved in CH2Cl2 and the reaction was monitored by TLC (EtOAc). After 4 hours, the starting material was consumed completely. The reaction mixture was extracted with CH2Cl2 and washed with 1N HCl, sat. NaHCO3 and brine, and purified by flash chromatography using EtOAc as eluent to yield 531 mg (68%) of benzyl 6-tosyl-6-deoxy-D-mannopyranoside.

Provenance & Evidence