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US 2025/0042930 A1Published application
Method for preparing aryl carbon glycoside compound including gliflozin drug
AssigneeSichuan University
InventorsDawen NIU, Xia ZHANG, Chen ZHANG, Hao ZUO, Hongxin ZENG, Yanjing LI, Jiaxi WANG
Life of this patent
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Abstract
In a method for preparing an aryl carbon glycoside compound including a gliflozin drug, a sulfinate glycosyl donor represented by formula W is used as a raw material to prepare the aryl carbon glycoside compound including the gliflozin drug. The method does not need to use an additional initiator.
Claims10
A method for preparing aryl C-glycosides, characterized in that the method comprises the following steps:
- a glycosyl donor represented by formula W, a glycosyl acceptor represented by formula B-1, Ni(II) catalyst, a photosensitizer, a ligand, and a base are added to a solvent, and then allowed to react under light, to obtain an aryl C-glycoside represented by formula B-2;
- wherein, n is selected from 0 or 1;
- a is selected from 3 or 4;
- R is each independently selected from L1Rx;
- alternatively, two adjacent R are linked to form a ring, and additional R is independently selected from L1Rx, wherein the ring is unsubstituted or substituted with one or more L1Rx;
- L1 is selected from absence or C1-2 alkylene;
- Rx is selected from the group consisting of H, hydroxyl, C1-6 alkyl, OAc, OBn, OR8, NR9R10,
- Ph, amino,
- i is an integer selected from 0 to 6;
- R11, R12, R13, and R14 are each independently selected from L2Ry;
- L2 is selected from absence or C1-2 alkylene, and Ry is selected from the group consisting of H, hydroxyl, C1-6 alkyl, OAc, OBn, OR8, and NR9R10;
- R8 is selected from C1-6 alkyl;
- R9 is selected from the group consisting of H, C1-6 alkyl, Ac, and Bn;
- R10 is selected from the group consisting of H, C1-6 alkyl, Ac, and Bn;
- j is 1, 2, or 3;
- Mj+ is a j-valent cation;
- X is halogen;
- Rb1 is selected from the group consisting of H, hydroxyl, C1-6 alkyl, C1-6 alkoxy, and halogen;
- Rb2 is selected from the group consisting of H and
- wherein ring A is selected from the group consisting of 5-6-membered aryl, 5-6 membered heteroaryl, fused cycloalkyl, or fused heterocyclic group;
- p is an integer from 0 to 2;
- Rb3 is each independently selected from the group consisting of C1-4 alkyl, C1-4 alkoxy, halogenated or unhalogenated phenyl, and ORb4, and Rb4 is selected from 5-6-membered saturated heterocyclic group or 5-6 membered saturated cycloalkyl.
19 more elements
Dependencies are inferred from the claim text.