Process for the specific synthesis of .beta.-glycosidically linked N-acetylpyranoside derivatives

• US 5,696,246 A
• Filed: 05/16/1996
• Issued: 12/09/1997
• Est. Priority Date: 05/16/1995
• Status: Expired due to Fees

• Current Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Original Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Inventors: Schmidt, Wolfgang, Kretzschmar, Gerhard
• Primary Examiner(s): Peselev, Elli
• Application Number:
  US08/648,717
• Time in Patent Office: 572 Days
• Field of Search: 536/18.5, 536/18.6
• US Class Current: 536/18.5
• CPC Class Codes: C07H 15/04 attached to an oxygen atom of the saccharide radical
• CPC Class Codes: C07H 15/26 Acyclic or carbocyclic radicals, substituted by hetero rings

Abstract

A process for the stereospecific synthesis of β-glycosidically linked N-acetylglucosamine derivatives is provided, wherein a protected α-(N-acetyl-2-amino-2-deoxy)-β-pyranosyl halide is coupled to a glycosyl acceptor using zinc chloride and a 4,4'"'"'-dialkoxytriphenylmethyl halide as catalysts.

Claims

1. A method for preparing an α

-(N-acetyl-2-amino-2-deoxy)-β

-pyranoside, comprising contacting a mixture of a protected α

-(N-acetyl-2-amino-2-deoxy)-α

-pyranosyl chloride and a glycosyl acceptor in a solvent with zinc chloride and a 4,4'"'"'-dialkoxytriphenylmethyl halide.

2. The method of claim 1, wherein the 4- and 4'"'"'-alkoxy groups of said 4,4'"'"'-dialkoxytriphenylmethyl halide are the same or different, and each is selected from the group consisting of methoxy-, ethoxy-, and isopropyloxy-.

3. The method of claim 2, wherein said 4,4'"'"'-dialkoxytriphenylmethyl halide is a 4,4'"'"'-dimethoxytriphenylmethyl halide, and wherein said halide atom is chloride, bromide, or iodide.

4. The method of claim 3, wherein said 4,4 '"'"'-dimethoxytriphenylmethyl halide 4,4'"'"'-dimethoxytriphenylmethyl chloride.

5. The method of claim 1, wherein said zinc chloride and said 4,4'"'"'-dialkoxytriphenylmethyl halide are employed in a molar ratio of about 1:

1.

6. The method of claim 1, wherein said solvent is dichloromethane.

7. The method of claim 1, wherein the hydroxyl groups of said protected α

-(N-acetyl-2-amino-2-deoxy)-β

-pyranosyl chloride are protected as esters.

8. The method of claim 7, wherein said esters are acetate esters.

9. The method of claim 7, wherein said protected N-acetyl-2-amino-2-deoxy-β

-pyranosyl chloride is a protected N-acetyl-2-amino-2-deoxy-β

-D-glucopyranosyl chloride.

10. The method of claim 9, wherein said protected N-acetyl-2-amino-2-deoxy-β

-D-glucopyranosyl chloride is N-acetyl-2-amino-2-deoxy-3,4,6-tri-O-acetyl-α

-D-glucopyranosyl chloride.