Method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose

• US 10,640,526 B2
• Filed: 11/16/2016
• Issued: 05/05/2020
• Est. Priority Date: 11/17/2015
• Status: Active Grant

• Current Assignee: Centre National De La Recherche Scientifique
• Original Assignee: Centre National De La Recherche Scientifique
• Inventors: Vauzeilles, Boris, Baron, Aurelie, Mas Pons, Jordi, Fourmois, Laura
• Primary Examiner(s): Berry, Layla D
• Application Number:
  US15/777,067
• Publication Number:
  US 20180319833A1
• Time in Patent Office: 1,266 Days
• Field of Search: None
• CPC Class Codes: C07H 1/00 Processes for the preparation of sugar derivatives
• CPC Class Codes: C07H 13/04 having the esterifying carboxyl radicals attached to acyclic carbon atoms
• CPC Class Codes: C07H 23/00 Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12 esters with inorganic acids C07H11/00; metal salts, see parent compounds
• CPC Class Codes: C07H 5/04 to nitrogen
• CPC Class Codes: C12Q 1/04 Determining presence or kind of microorganism; Use of selective media for testing antibiotics or bacteriocides; Compositions containing a chemical indicator therefor C12Q1/6897 takes precedence

Abstract

Disclosed is a method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose. This method includes the chemical reaction of compound of formula X:

Wherein: R¹ can be a C₁ to C₆ alkyl including methyl, ethyl, isopropyl; aryl including phenyl; each of these groups being substituted or not; and R² can be a C₁ to C₆ alkyl including methyl, ethyl, isopropyl, tert-butyl, isobutyl; each of these groups being substituted or not; with a deprotecting reagent including a Lewis or Brönsted acid in a polar aprotic solvent, thereby obtaining a free C-1 OH group. The method can also start with the preparation from commercially available D-galactose pentaacetate, D-galactose tetraacetate or tetraacetyl D-galactosyl trichloroacetimidate. The step of deprotecting the anomeric position avoids the use of cerium and allows the easy purification of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose.

Claims

1. A method of making 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose:

2. The method according to claim 1, wherein the compound of formula X is 1′

-trimethylsilylethanyl 6-azido-2,4-diacetamido-2,4,6-trideoxy-β

-D-mannopyranoside;

3. The method according to claim 1, wherein the compound of formula X is made by reacting a compound of formula IX:

4. The method according to claim 3, wherein the compound of formula IX is 1′

-trimethylsilylethanyl 2,4-diacetamido-2,4-dideoxy-6-O-mesyl-β

-D-mannopyranoside;

5. The method according to claim 3, wherein the compound of formula IX is made by reacting a compound of formula VIII:

6. The method according to claim 5, wherein the compound of formula VIII is 1′

-trimethylsilylethanyl 2,4-diacetamido-2,4-dideoxy-β

-D-mannopyranoside;

7. The method according to claim 5, wherein the compound of formula VIII is made by reacting a compound of formula VII:

8. The method according to claim 7, wherein the compound of formula VII is 1′

-trimethylsilylethanyl 2,4-diazido-2,4-dideoxy-β

-D-mannopyranoside;

9. The method according to claim 7, wherein the compound of formula VII is made by reacting a compound of formula VI:

10. The method according to claim 9, wherein the reagent for deprotection of ester groups is sodium methanolate or potassium carbonate.

11. The method according to claim 9, wherein the compound of formula VI is made by reacting a compound of formula V:

12. The method according to claim 11, wherein the compound of formula V is made by reacting a compound of formula IV:

13. The method according to claim 12, wherein the compound of formula IV is made by reacting a compound of formula III:

14. The method according to claim 13, wherein the reagent for deprotection of ester groups is sodium methanolate or potassium carbonate.

15. The method according to claim 13, wherein the compound of formula III is made by reacting O-(2,3,4,6-tetra-O-acetyl-β

-D-galactopyranosyl)trichloroacetimidate;

16. The method according to claim 15, wherein the 0-(2,3,4,6-tetra-O-acetyl-β

-D-alactopyranosyl) trichloroacetimidate is made by reacting 2,3,4,6-tetra-O-acetyl-D-galactopyranose;

17. A method of making 6-azido-2,4-diacetamido-2,4,6-trideoxy-d-mannose:

18. A compound selected from the group consisting of:

19. A compound of formula VIII:

20. A compound selected from the group consisting of: