US 12,454,543 B2
Process for production of ascarylose and related compounds
James Eagan, Ithaca, NY (US)
Assigned to Ascribe Bioscience Inc., Ithaca, NY (US)
Appl. No. 18/007,435
Filed by Ascribe Bioscience Inc., Ithaca, NY (US)
PCT Filed Jul. 30, 2021, PCT No. PCT/IB2021/056981
§ 371(c)(1), (2) Date Jan. 30, 2023,
PCT Pub. No. WO2022/024067, PCT Pub. Date Feb. 3, 2022.
Claims priority of provisional application 63/059,363, filed on Jul. 31, 2020.
Prior Publication US 2023/0279040 A1, Sep. 7, 2023
Int. Cl. C07H 15/04 (2006.01); C07H 15/10 (2006.01); C07H 15/207 (2006.01)
CPC C07H 15/207 (2013.01) [C07H 15/04 (2013.01); C07H 15/10 (2013.01)] 29 Claims
 
1. A method for the production of 1-O-substituted ascarylose, comprising:
providing as a feedstock a 1-O-substituted rhamnose having the structure of Formula II, wherein Z is a non-hydrogen substituent;

OG Complex Work Unit Chemistry
forming a mono-sulfonate ester at the 3-OH group of the feedstock; and
treating the mono-sulfonate ester with a hydride source to form the 1-O-substituted ascarylose,
wherein forming the mono-sulfonate ester is conducted on the 1-O-substituted rhamnose without hydroxyl protecting groups at either the 2-OH or 4-OH-positions.