Glycosyl donor, preparation method therefor, and use thereof
AssigneeSichuan University
InventorsDawen NIU, Xia ZHANG, Liqiang WAN, Chen ZHANG, Demeng XIE
Life of this patent
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Abstract
A glycosyl donor represented by formula (I) is used for preparing an S-glycoside compound represented by formula (III), an O-glycoside compound represented by formula (V), and a C-glycoside compound represented by formula (V). The glycosyl donor is a raw material in the preparation of O-glycoside, S-glycoside, and C-glycoside compounds by means of a free radical reaction, most of which have a special α configuration.
Claims14
A S-glycoside compound, or a salt thereof, or a stereoisomer thereof, or an optical isomer thereof, wherein said S-glycoside compound has a structure of formula III:
- wherein, R10 is selected from
- substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl,
- the group obtained by removing a hydrogen from the peptide chain;
- said substituent is selected from halogen, haloalkyl;
- m denotes an integer of 1-4;
- Y is selected from none, NH or O;
- each of R1a and R2a is independently selected from the group consisting of H, Boc, Bz, C1-6 alkyl, C1-6 alkoxyl, aryl, heteroaryl, the group obtained by removing a hydrogen from the peptide chain,
- wherein each of m1 and m2 is independently selected from an integer of 0-5;
- Ra1 is selected from substituted or unsubstituted C1-6 alkyl;
- said substituent is selected from halogen and hydroxyl;
- Ra3 is selected from substituted or unsubstituted C1-6 alkyl, aryl, heteroaryl;
- said substituent is selected from halogen and hydroxyl;
- Ring A is selected from
- each of R1, R2, R3, and R4 is independently selected from the group consisting of H, C1-6 alkyl, aryl or heteroaryl substituted C1-12 alkyl, C1-12 alkoxyl, C2-8 alkynyl, C2-8 alkenyl, aryl, heteroaryl, cycloalkyl, M1OH, M1NH2, M1NHAc, M1OAc, M1OBz, M1OBn, M1N3, M1OTMS, M1OTBS,
- or any two of R1, R2, R3, and R4 are linked to form a ring;
- M1 is selected from 0-3 methylene;
- M2, M3, M4 are selected from the group consisting of H, C1-6 alkyl, aryl or heteroaryl substituted C1-12 alkyl, C2-8 alkynyl, C2-8 alkenyl, aryl, heteroaryl;
- or M3 and M4 are linked to form a ring;
An O-glycoside compound, or a salt thereof, or a stereoisomer thereof, or an optical isomer thereof, wherein said O-glycoside compound has a structure of formula IV:
- wherein, R11 is selected from L0R12 or COL0R12;
- L0 is selected from 0-3 alkylene, R12 is selected from substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted ring;
- said substituent is one or more, and each of said substituents is independently selected from CN, C1-6 alkoxyl, C1-6 alkoxyl, Li(COOEt)NHBz, OH, NH2, NHAc, OAc, OBz, OBn;
- Li is selected from 0-3 alkylene;
- ring A is selected from
- each of R1, R2, R3, and R4 is independently selected from the group consisting of H, C1-6 alkyl, aryl or heteroaryl substituted C1-12 alkyl, C1-12 alkoxyl, C2-8 alkynyl, C2-8 alkenyl, aryl, heteroaryl, cycloalkyl, M1OH, M1NH2, M1NHAc, M1OAc, M1OBz, M1OBn, M1N3, M1OTMS, M1OTBS,
- or any two of R1, R2, R3, and R4 are linked to form a ring;
- M1 is selected from 0-3 methylene;
- M2, M3, M4 are selected from the group consisting of H, C1-6 alkyl, aryl or heteroaryl substituted C1-12 alkyl, C2-8 alkynyl, C2-8 alkenyl, aryl, heteroaryl;
- or M3 and M4 are linked to form a ring.
A C-glycoside compound, or a salt thereof, or a stereoisomer thereof, or an optical isomer thereof, wherein said C-glycoside compound has a structure of formula V:
- wherein, ring A is selected from
- each of R1, R2, R3, and R4 is independently selected from the group consisting of H, C1-6 alkyl, aryl or heteroaryl substituted C1-12 alkyl, C1-12 alkoxyl, C2-8 alkynyl, C2-8 alkenyl, aryl, heteroaryl, cycloalkyl, M1OH, M1NH2, M1NHAc, M1OAc, M1OBz, M1OBn, M1N3, M1OTMS, M1OTBS,
- or any two of R1, R2, R3, and R4 are linked to form a ring;
- M1 is selected from 0-3 methylene;
- M2, M3, M4 are selected from the group consisting of H, C1-6 alkyl, aryl or heteroaryl substituted C1-12 alkyl, C2-8 alkynyl, C2-8 alkenyl, aryl, heteroaryl;
- or M3 and M4 are linked to form a ring;
- is
- ring B is saturated or unsaturated ring, and preferably is benzene ring;
- R14 is selected from H, CN, halogenated or unhalogenated C1-3 alkyl, halogenated or unhalogenated C1-3 alkoxyl, COOR15;
- R15 is selected from C1-3 alkyl.
Dependencies are inferred from the claim text.