Syntheses of D-chiro-3-inosose and (+)-D-chiro inositol

• US 5,602,287 A
• Filed: 03/24/1995
• Issued: 02/11/1997
• Est. Priority Date: 10/05/1992
• Status: Expired due to Term

• Current Assignee: Virginia Tech Intellectual Properties, Inc. (Virginia Polytechnic Institute and State University)
• Original Assignee: Virginia Tech Intellectual Properties, Inc. (Virginia Polytechnic Institute and State University)
• Inventors: Hudlicky, Tomas, Mandel, Martin
• Primary Examiner(s): Chan, Nicky
• Application Number:
  US08/410,611
• Time in Patent Office: 690 Days
• Field of Search: 568/833
• US Class Current: 568/833
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 29/145 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 35/16 Inositols
• CPC Class Codes: C07D 317/46 condensed with one six-membered ring
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C07D 493/14 Ortho-condensed systems

Abstract

There are described novel biocatalytic and chemical processes for the synthesis of various oxygenated compounds. Particularly, there are described processes for the synthesis of a useful synthon 12 made by reacting a protected diol (acetonide) with permaganate under appropriate conditions. Such synthon is useful of the synthesis of various pharmaceutically important compounds such as D-chiro-inositol and D-chiro-3-inosose. Also, there are disclosed novel compounds, including specifically the synthon 12 and compounds derived therefrom.

Claims

1. A process for preparing D-chiro-inositol 6 comprising reducing D-chiro-3-inosose 10 with a reducing agent selected from the group consisting of zinc borohydride and sodium borohydride at a temperature between about -10°

C. to about 110°

C., in acetonitrile.

2. A process of claim 1 wherein the temperature is between about 50°

C. to about 100°

C.