US 12,404,293 B2
Method for producing glycan, building block for gylican synthesis, and compound
Toshiki Nokami, Tottori (JP); Toshiyuki Itoh, Tottori (JP); Hiraku Sakai, Tokyo (JP); and Tomoaki Hamada, Tokyo (JP)
Assigned to NATIONAL UNIVERSITY CORPORATION TOTTORI UNIVERSITY, Tottori (JP); and KOGANEI CORPORATION, Tokyo (JP)
Appl. No. 17/434,331
Filed by NATIONAL UNIVERSITY CORPORATION TOTTORI UNIVERSITY, Tottori (JP); and KOGANEI CORPORATION, Tokyo (JP)
PCT Filed Feb. 25, 2020, PCT No. PCT/JP2020/007365
§ 371(c)(1), (2) Date Mar. 11, 2022,
PCT Pub. No. WO2020/175440, PCT Pub. Date Sep. 3, 2020.
Claims priority of application No. 2019-035709 (JP), filed on Feb. 28, 2019.
Prior Publication US 2023/0143273 A1, May 11, 2023
Int. Cl. C07H 3/06 (2006.01); C07D 309/04 (2006.01); C07H 3/02 (2006.01)
CPC C07H 3/06 (2013.01) [C07D 309/04 (2013.01); C07H 3/02 (2013.01)] 13 Claims
 
1. A method for producing a glycan, the method comprising:
subjecting a building block A, which is at least one building block selected from a building block represented by Formula (1) below, or a building block that contains a sugar residue derived from the building block represented by Formula (1) below and a sugar residue derived from a building block represented by Formula (2) below, to electrolytic oxidation in an aprotic organic solvent that contains an electrolyte;
subjecting a building block B, which is at least one building block selected from a building block represented by Formula (2) below, or a building block that contains a plurality of sugar residues derived from the building block represented by Formula (2), to glycosylation with the electrolytically oxidized building block A; and
further repeating a sequence of the electrolytic oxidation and the glycosylation;
wherein the produced glycan is a polysaccharide equal to longer than trisaccharide;

OG Complex Work Unit Chemistry
in Formula (1),
A1 represents a cyclic structure having 4 to 8 carbon atoms;
each of Z1 to Z5 independently represents a hydrogen atom or an electron attractive group, with the total of the Hammett's σ values of Z1 to Z5 exceeding 0.12;
L1 represents a single bond or a divalent linking group;
each of R1 and R2 independently represents a monovalent organic group;
each of m (R1)s and n (R2)s may bind to each other to form a ring;
m represents an integer of 0 or larger, n represents an integer of 1 or larger;
m+n is equal to or smaller than the number of carbon atoms of the cyclic structure A1;
each wavy line independently represents a bond in the equatorial or axial conformation;

OG Complex Work Unit Chemistry
in Formula (2),
A2 represents a cyclic structure having 4 to 8 carbon atoms;
each of Z6 to Z10 independently represents a hydrogen atom or an electron attractive group, with the total of the Hammett's σ values of Z6 to Z10 exceeding 0.12;
L2 represents a single bond or a divalent linking group;
R3 represents a monovalent organic group,
R4 represents a hydrogen atom or a monovalent organic group, at least one of q (R4)s represents a hydrogen atom;
each of p (R3)s and q (R4)s may bind to each other to form a ring,
p represents an integer of 0 or larger, q represents an integer of 1 or larger;
p+q is equal to or smaller than the number of carbon atoms of the cyclic stricture A2; and
each wavy line independently represents a bond in the equatorial or axial conformation,
wherein at least one of Z1 to Z5 represents chlorine atom, and
at least one of Z6 to Z10 represents chlorine atom.