IP Library Granted Patent US 8,461,359
Granted Patent B2
US 8,461,359 · App. 13/119,332 · Granted Jun 11, 2013

Short synthetic pathway for 1,6:2,3-dianhydro-β-D-mannopyranose

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Quick Facts
Patent No.
US 8,461,359
App. No.
13/119,332
Granted
Jun 11, 2013
Kind
B2
Abstract

The invention relates to a method for preparing 1,6:2,3-dianhydro-β-D-mannopyranose and is characterized in that it includes a step of cyclizing the compound B, where R is an activating agent, in the presence of a base selected from among ammonium hydroxides and mineral bases.

Claims (17)

1. A process for the preparation of compound (I):

characterized in that it comprises a stage of cyclisation of compound B:

in which R represents an activating group, in the presence of a base chosen from ammonium hydroxides and inorganic bases.

2. The process according to claim 1 , wherein said base is chosen from an ammonium hydroxide, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate or caesium carbonate.

3. The process according to claim 1 , wherein said base is tetrabutylammonium hydroxide.

4. The process according to claim 1 , wherein said base is caesium carbonate.

5. The process according to claim 1 , wherein the cyclisation stage is carried out in isopropanol, dichloromethane or acetonitrile, or in a binary mixture thereof.

6. The process according to claim 3 , wherein the cyclisation stage is carried out in an isopropanol/dichloromethane mixture.

7. The process according to claim 6 , wherein the cyclisation stage is carried out at a temperature of between −10° C. and 0° C.

8. The process according to claim 4 , wherein the cyclisation stage is carried out in acetonitrile.

9. The process according to claim 8 , wherein the cyclisation stage is carried out at a temperature of approximately 40° C.

10. The process according to claim 1 , wherein compound B is such that R represents a tosyl, mesyl, benzenesulphonyl or p-halobenzenesulphonyl group.

11. The process according to claim 1 , comprising:

a stage of activation of compound A:

to obtain compound B,

followed by the stage of cyclisation of compound B.

12. The process according to claim 11 , wherein the stage of activation of compound A is carried out using a tosyl, mesyl, benzenesulphonyl or p-halobenzenesulphonyl halide.

Assignments (2)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2011
From: BOUVENOT, LAURENT; CRUCIANI, PAUL; LARGEAU, DENIS; ROVERA, JEAN-CLAUDE
To: SANOFI-AVENTIS
Reel/Frame 026246/0292 →