Boron trifluoride etherate → 5-ethoxycarbonylpentyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside

Participants

Reaction Steps

To mannose pentaacetate (10.00 g, 25.64 mmol) dissolved in 60 mL of CH2Cl2, ethyl 6-hydroxyhexanoate (8.3 mL, 51.28 mmol) was added at room temperature and then BF3.Et2O at 0° C. After 4 days under stirring at room temperature, the reaction mixture was washed twice with NaHCO3 (2×20 mL) and then with brine (20 mL). The organic layer was dried (MgSO4) and concentrated under vacuum. Compound 1 (7.14 g, 57%) was obtained after column chromatography on silica gel (hexane/AcOEt; 6:4).

Provenance & Evidence