US 12,291,547 B2
Synthesis of 3-azido-3-deoxy-D-galactopyranose
Denis Giguère, Saint-Augustin-de-Desmaures (CA); Jacob St-Gelais, Longueuil (CA); and Vincent Denavit, Feugarolles (FR)
Assigned to UNIVERSITÉ LAVAL, Quebec (CA)
Appl. No. 17/615,724
Filed by UNIVERSITÉ LAVAL, Quebec City (CA)
PCT Filed Jun. 12, 2020, PCT No. PCT/CA2020/050814
§ 371(c)(1), (2) Date Dec. 1, 2021,
PCT Pub. No. WO2020/248068, PCT Pub. Date Dec. 17, 2020.
Claims priority of provisional application 62/861,476, filed on Jun. 14, 2019.
Prior Publication US 2022/0251129 A1, Aug. 11, 2022
Int. Cl. C07H 1/00 (2006.01); C07H 5/04 (2006.01); C07H 13/08 (2006.01); C07H 19/056 (2006.01)
CPC C07H 1/00 (2013.01) [C07H 5/04 (2013.01); C07H 13/08 (2013.01); C07H 19/056 (2013.01)] 19 Claims
 
1. A method for synthesizing a 3-azido-3-deoxy-D-galactopyranose of formula IV

OG Complex Work Unit Chemistry
said method comprising:
(a) epoxidation of a compound of formula II to form a compound of formula III

OG Complex Work Unit Chemistry
where R is an activating group; and
(b) ring opening of the epoxide of the compound of formula III with an inorganic or organic azide to produce the compound of formula IV;
wherein the activating group is a sulfonyl, trifluoromethanesulfonyl, or imidazole-1- sulfonyl.