# US 8,569,467 B2 · C-glycoside compounds, and method for preparing C-glycoside compounds

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- Number: US 8,569,467 B2
- Document ID: US8569467B2
- Status: Granted
- Kind: B2
- Application number: 13/127,380
- Filed: 2009-11-06
- Published: 2011-10-06
- Granted: 2013-10-29
- Earliest claimed: 2008-11-07
- Assignees: Ecole Nationale Superieure De Chimie De Rennes; Armor Proteines
- Applicants: Thierry Benvegnu; Loïc Lemlegre; Adeline Ranoux
- Inventors: Thierry Benvegnu; Loïc Lemlegre; Adeline Ranoux
- Web page: https://patentgrep.com/patent/US8569467B2

## CPC

- C07H 1/00: Processes for the preparation of sugar derivatives
- C07H 7/00: Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

The invention relates to C-glycose compounds of formula (I) where: S′ is a monosaccharide radical or a polysaccharide radical derived from a monosaccharide or polysaccharide S; R is a linear or branched alkyl radical; and Z is an ethylenyl CH═CR1(R2) or an acetylenyl C≡CR3 radical. The invention also relates to a method for preparing C-glycoside compounds of formula (III), characterized in that the method consists of a step of reacting a sugar (S), in an aqueous solvent or in the absence of a solvent and in the presence of an organic or mineral base (B), with a phosphonate of formula (II) according to the following reaction pattern: Formulas (II), (III).

## Claims

### Claim 1

C-glycoside compound, characterised in that it has the following formula (I):
where:
S′ represents a monosaccharide radical, or polysaccharide radical having up to 20 sugar units, in pyranose and/or furanose form and of series L and/or D:
the bond S′—CH2C(OH) represents a bond of a C-anomeric nature;
R represents a linear or branched alkyl radical able to have one or more insaturations and comprising 1 to 30 carbon atoms; and
Z represents an ethylenyl radical CH═CR1(R2) or acetylenyl radical C≡CR3 such that R1, R2 and R3 represent independently a hydrogen atom or a linear or branched alkyl radical, which may have one or more insaturations and comprising 1 to 30 carbon atoms.

### Claim 2 (depends on 1)

Compound according to claim 1, in which said radical S′ is chosen from the group consisting of the radicals: glucosyl, galactosyl, mannosyl, xylosyl, lactosyl, N-acetyl-glucosaminosyl, and N-acetyl-galactosaminosyl.

### Claim 3 (depends on 2)

Compound according to claim 2, in which said radical S′ is chosen from the group formed by the radicals: lactosyl, glucosyl, xylosyl.

### Claim 4 (depends on 1)

Compound according to claim 1, characterised in that Z represents a CH═CH2 radical.

### Claim 5

Method of preparing C-glycoside compounds of the tertiary alcohol type of formula (I) including a step of making a C-glycoside compound of formula (III′) react in an aqueous solvent and in the presence of a metal (M), with a halogenated compound of formula (IV) according to the following reaction diagram:
where:
S′ represents a monosaccharide radical, or a polysaccharide radical having up to 20 sugar units, in pyranose and/or furanose form and of series L and/or D;
the bond S′—C H2C(O) represents a bond of C-anomeric nature;
R represents a linear or branched alkyl radical that may have one or more insaturations and comprising 1 to 30 carbon atoms;
Z represents an ethylenyl radical CH═CR1(R2) or acetylenyl radical C≡CR3 such that R1, R2 and R3 represent independently a hydrogen atom or a linear or branched alkyl radical, which may have one or more insaturations and comprising 1 to 30 carbon atoms;
M represents a metal chosen from indium, zinc or magnesium;
and X represents a halogen.

### Claim 6 (depends on 5)

Method according to claim 5, characterised in that it comprises the steps consisting of:
dissolving an equivalent of said C-glycoside compound of formula (III′) in a sufficient quantity of water;
adding between 1 and 4 equivalents of said halogenated compound of formula (IV) and between 1 and 4 equivalents of metal (M) at a temperature of between 20° C. and 40° C. over a period of between 3 hours and 30 hours; and
co-evaporating the aqueous phase with an organic solvent chosen from the group formed by ethanol, methanol, toluene and/or isopropanol,
or drying,
or freeze drying.

### Claim 7

Method of preparing C-glycoside compounds of the tertiary alcohol type of formula (I) comprising making a monosaccharide or a polysaccharide S react with a phosphonate of formula (II′) in the presence of water, a metal (M) with a halogenated compound of formula (IV), in accordance with following reaction diagram:
where:
S represents a monosaccharide or a polysaccharide having up to 20 sugar units, in pyranose and/or furanose form and of series L and/or D, said mono- or polysaccharide having at least one free hydroxyl function;
S′ represents a monosaccharide radical, or polysaccharide radical having up to 20 sugar units, in pyranose and/or furanose form and of series L and/or D derived from said monosaccharide or polysaccharide S;
the bond S′—CH2C(OH) represents a bond of C-anomeric nature;
R4 and R4′ represent independently a linear or branched alkyl radical comprising 1 to 6 carbon atoms;
R represents a linear or branched alkyl radical, which may have one or more insaturations and comprising 1 to 30 carbon atoms;
X represents a halogen,
Z represents an ethylenyl function CH═CR1(R2) or acetylenyl function C≡CR3 such that R1, R2 and R3 represent independently a hydrogen or a linear or branched alkyl radical, which may have one or more insaturations and comprising 1 to 30 carbon atoms; and
M represents a metal chosen from indium, zinc or magnesium; and
B is an organic or mineral base.

### Claim 8 (depends on 7)

Method according to claim 7, characterised in that it includes the steps consisting of:
dissolving an equivalent of said monosaccharide or polysaccharide S in a sufficient quantity of water;
adding between 1 and 5 equivalents, of phosphonate of formula (II′), and between 1 and 10 equivalents, of base B, at a temperature of between 25° C. and 100° C., over a period of between 3 hours and 30 hours;
adding between 1 and 4 equivalents of said halogenated compound of formula (IV) and between 1 and 4 equivalents of metal (M) at a temperature of between 20° C. and 40° C. over a period of between of between 3 hours and 30 hours; and
co-evaporating the aqueous phase with an organic solvent chosen from the group consisting of ethanol, methanol, toluene and/or isopropanol,
or drying,
or freeze drying.