Water → (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-one

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Reaction Steps

27 g of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (50 mmol) was dissolved in 153 mL of DMSO to form a clear solution. 102 mL of acetic anhydride was added dropwise. The resultant clear solution was allowed to stir at room temperature overnight. After 17 hours, GC-MS showed the lactone was gone and a new compound was observed. The yellow solution was poured into 600 mL of water and sat in a separation funnel overnight. The precipitated oil was passed through a silica gel column, eluted first with cyclohexane then gradually increasing polarity by adding acetone until the final eluent was cyclohexane: acetone=2:1. The appropriate portions were collected and evaporated to give a pale syrup. 25.2 g, yield: 94%. IR (v cm−1) 2867,1752.

Provenance & Evidence