	US 12,234,255 B2
	Methods for glycosylation
John Montgomery, Ann Arbor, MI (US); Girish Chandra Sati, Ann Arbor, MI (US); and Joshua Lane Martin, Ann Arbor, MI (US)
Assigned to REGENTS OF THE UNIVERSITY OF MICHIGAN, Ann Arbor, MI (US)
Appl. No. 17/610,996
Filed by THE REGENTS OF THE UNIVERSITY OF MICHIGAN, Ann Arbor, MI (US)
PCT Filed May 14, 2020, PCT No. PCT/US2020/032793 § 371(c)(1), (2) Date Nov. 12, 2021, PCT Pub. No. WO2020/232194, PCT Pub. Date Nov. 19, 2020.
Claims priority of provisional application 62/847,587, filed on May 14, 2019.
Prior Publication US 2022/0267362 A1, Aug. 25, 2022
Int. Cl. C07H 1/00 (2006.01); C07F 7/18 (2006.01); C07H 15/10 (2006.01); C07H 15/18 (2006.01); C07H 15/203 (2006.01)

CPC C07H 1/00 (2013.01) [C07F 7/1804 (2013.01); C07H 15/10 (2013.01); C07H 15/18 (2013.01); C07H 15/203 (2013.01)]

22 Claims

1. A method comprising admixing at least one fluoroglycoside of formula (I) and a silyl ether glycoside, in the presence of a catalyst having a formula B (Ar¹)(Ar²)(Ar³) under conditions sufficient to form a glycoside product:

wherein

each of R², R³, R⁴, and R⁶is independently H, C_1-6alkyl, —N(R¹)₂, —N₃, CO₂H, CO₂C_1-6alkyl, or —OR^PG, or

two of R², R³, R⁴, and R⁶, together with the atoms to which they are attached form a five to eight membered heterocycloalkyl having 1 to 3 ring heteroatoms selected from O, N, and S;

each of Ar¹, Ar², Ar³is independently a halophenyl;

each R¹is independently H, C(O)C_1-6alkyl, or an amino protecting group;

m is 0 or 1; and

each R^PGis independently a hydroxyl protecting group or a saccharide.