(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-one → HCID 11330356, compound

Participants

Reaction Conditions

Reaction Steps

18 g (33 mmol) of 21a was dissolved in 200 mL of anhydrous THF under nitrogen. Cooled to −78° C. 45 mL of MeLi (1.6 M, 72 mmol) was added by a syringe. After 1 hour at −78° C., the reaction was quenched by a solution of 7 g of NH4Cl in 200 mL of H2O. TLC showed no starting material left, while a new spot corresponding to the product appeared. The mixture was extracted by 3×150 mL of ethyl acetate, washed by brine, dried over Na2SO4. After evaporation, a thick pale yellow oil was obtained which was turned into a white solid (17.6 g, 95% yield) with a melting point of 92–93° C. 300 MHz 1H NMR(CDCl3) δ: 1.41 (s, 3H, CH3); 2.58 (s, 1H, OH); 3.35–3.38 (d, 1H); 3.65–3.72 (m, 3H); 3.93–3.99 (m, 2H); 4.50–4.95 (m, 8H, 4-CH2), 7.14–7.36 (m, 20H). 13C NMR (CDCl3) δ: 26.59, 68.81, 71.55, 73.42, 74.85, 75.58, 75.68, 78.42, 83.18, 83.63, 97.36, 127.58, 127.65, 127.74, 127.82, 127.84, 127.91, 128.28, 128.32, 128.36, 128.41, 137.87, 138.21, 138.25, 138.64.

Provenance & Evidence