(2-Ethyl 2,3,4-Tri-O-acetyl--D-glucopyranoside) Uronate synthesis

Yield:77392-66-6 83%

Reaction Conditions:

with silver carbonate in toluene at 20 - 75; for 21 h;Inert atmosphere;Koenigs-Knorr synthesis;

Steps:

1.2. General procedure for the synthesis of protected short-chain alkyl glucopyranuronates

General procedure: To a stirred solution of methyl (2,3,4-tri-O-acetyl-α-d-glucopyranosyl)uronate bromide (3) in dry toluene under Argon atmosphere the corresponding dried alcohol was added and the solution was warmed to 75 °C. Subsequently, silver carbonate was added in three portions over a period of 3 h. Then the reaction was stirred at room temperature for 18 h. Afterwards, the suspension was filtered and the filtrate was evaporated to dryness. Purification by flash chromatography (silica gel, cyclohexane-ethyl acetate 1:1) or recrystallisation from i-propanol gave the product 4.

References:

M?nch, Bettina;Gebert, Antje;Emmerling, Franziska;Becker, Roland;Nehls, Irene [Carbohydrate Research,2012,vol. 352,p. 186 - 190] Location in patent:experimental part