Trityl chloride → HCID 11386706, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3 (6 g)-and freshly purified chlorotriphenylmethane (5 g) in dry pyridine (50 mL) was heated for 2 hrs at 80° C. and then cooled to 0° C. 3-O-benzyl-6-O-triphenylmethyl-D-glucopyranose (16) could be isolated at this stage, or used further for acetylation. Acetic anhydride (15 mL)-was added, and the reaction mixture was heated at 80° C. until compound 16 had disappeared (TLC, ether:hexane, 1:2). The mixture was concentrated and a solution of the residue in chloroform (100 mL) was washed with aqueous potassium hydrogen sulfate and water, and concentrated. The crude 3-O-benzyl-6-O-triphenylmethyl-1,2,4-tri-O-acetyl-D-glucopyranose (17) was used in the next reaction. Small scale chromatography gave a material with 1H NMR data: 60:40 mixture of alpha:beta anomers 7.19-7.44 (m, 20 H, arom), 6.42 (d, 1 H, alpha-H)-, 5.67 (d, 1 H, beta-H), 3.07-5.23 (8 H), 2.17 (s, 3 H, Ac-alpha), 2.16 (s, 3H, Ac-beta) 2.01 (s, 3 H Ac-α, 1.99 (s, 3 H, Ac-beta), 1.69 (s, 3 H, Ac-β), 1.66 (s, 3 H, Ac-alpha).

Provenance & Evidence