# US 2013/0158242 A1 · Alpha-selective glycosylation method

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- Number: US 2013/0158242 A1
- Document ID: US20130158242A1
- Status: Published application
- Kind: A1
- Application number: 13/525,696
- Filed: 2012-06-18
- Published: 2013-06-20
- Earliest claimed: 2011-12-16
- Assignees: National Chiao Tung University
- Inventors: Kwok-Kong Tony Mong; Chin-Sheng Chao; Shao-Ru Lu; Chih-Yueh Liu
- Web page: https://patentgrep.com/patent/US20130158242A1

## CPC

- C07H 1/00: Processes for the preparation of sugar derivatives
- C07H 15/18: Acyclic radicals, substituted by carbocyclic rings
- 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 present invention provides an α-selective glycosylation method. The α-selective glycosylation method includes performing a reaction of a donor having a saccharide structure and a formamide-containing compound to form a glycosyl imidate compound; and in one pot environment, performing an addition reaction of the glycosyl imidate compound and an acceptor having a hydroxyl group to form an α-glycoside with high α-selectivity. The α-selective glycosylation method is applicable to the large scale production and easy to recover the formamide-containing compound.

## Claims

### Claim 1

An α-selective glycosylation method, comprising the steps of:
performing a reaction of a donor having a saccharide structure and a formamide-containing compound to form a glycosyl imidate compound; and
performing a coupling reaction of the glycosyl imidate compound with an acceptor having a hydroxyl group to form an α-glycoside.

### Claim 2 (depends on 1)

The α-selective glycosylation method of claim 1, wherein a carbon atom at the first position of the saccharide structure has a substitute, and the substitute is activated by an activating agent.

### Claim 3 (depends on 2)

The α-selective glycosylation method of claim 2, wherein the carbon atom at the first position of the saccharide structure is substituted with a thioacetal group, and the activating agent is a halonium ion source.

### Claim 4 (depends on 2)

The α-selective glycosylation method of claim 2, wherein the halonium ion source is a mixture of N-halosuccinimide and a Lewis acid.

### Claim 5 (depends on 4)

The α-selective glycosylation method of claim 4, wherein the N-halosuccinimide is iodosuccinimide or bromosuccinimide, and the Lewis acid is triflic acid, trimethylsilyl triflate or silver triflate.

### Claim 6 (depends on 1)

The α-selective glycosylation method of claim 1, wherein a carbon atom oat the first position of the saccharide structure is substituted with a thioacetal, a halo, a phosphate or an acetimidate.

### Claim 7 (depends on 6)

The α-selective glycosylation method of claim 6, wherein the thioacetal is thiotoluenyl acetal or thiophenyl acetal.

### Claim 8 (depends on 6)

The α-selective glycosylation method of claim 6, wherein the acetimidate is trichloroacetimidate or N-phenyl trifluoroacetimidate.

### Claim 9 (depends on 6)

The α-selective glycosylation method of claim 6, wherein the phosphate is diphenyl phosphate.

### Claim 10 (depends on 6)

The α-selective glycosylation method of claim 6, wherein the saccharide structure has an active atom with a protecting group, and the active atom is O or N.

### Claim 11 (depends on 1)

The α-selective glycosylation method of claim 1, wherein the saccharide structure has 6 or more carbon atoms.

### Claim 12 (depends on 11)

The α-selective glycosylation method of claim 11, wherein the saccharide structure is a linear or circular structure.

### Claim 13 (depends on 1)

The α-selective glycosylation method of claim 1, wherein the donor is D-galactose, D-glucose, 2-azido-2-deoxy-D-galactose, 2-azido-2-deoxy-D-glucose, L-idopyranose, D-mannose, or L-rhamnose.

### Claim 14 (depends on 1)

The α-selective glycosylation method of claim 1, wherein the formamide-containing compound has a structure of formula (I):
wherein R1 and R2 are independently C1-C6alkyl or R1 and R2 are part of a 5-membered or 6-membered heterocyclic compound that bears one or more heteroatoms.

### Claim 15 (depends on 14)

The α-selective glycosylation method of claim 14, wherein the heterocyclic compound has at least one carbon atom replaced by an oxygen atom.

### Claim 16 (depends on 14)

The α-selective glycosylation method of claim 14, wherein the formamide-containing compound is N,N-dimethylformamide, N,N-diethylformamide, N,N-diisopropylformamide, N-formylpyrrolidine, N-formylpiperidine or N-formylmorpholine.

### Claim 17 (depends on 1)

The α-selective glycosylation method of claim 1, further comprising the steps of:
activating the α-glycoside to react with the formamide-containing compound; and
performing a coupling reaction with the acceptor having the hydroxyl group.