Fluorinated cyclitols. An improved synthesis of 5-deoxy-5-fluoro-myo-inositol, its deuterium labeling, and synthesis of a 5,5-gem-difluoro analogue
✍ Scribed by Cong Jiang; David J.A. Schedler; Philip E. Morris Jr.; Abdel-Hadi A. Zayed; David C. Baker
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- English
- Weight
- 688 KB
- Volume
- 207
- Category
- Article
- ISSN
- 0008-6215
No coin nor oath required. For personal study only.
✦ Synopsis
An improved synthesis of S-deoxy-5-fluoro-myo-inositol is provided via the reaction of diethylaminosulfur trifluoride (DAST) with the versatile intermediate, 1,4,6-tri-O-benzyl-2,3-O-cyclohexylidene-neoinositol (I), followed by appropriate deprotection reactions. Reaction of DAST with the 5-keto analogue of I gave the gem-difluoro compound, which upon deprotection afforded S-deoxy-5,5-difluoro-myo-inositol.
A 'H-n.m.r. study of the deuteration of 5-deoxy-5-fluoro-myo-inositol with Raney nickeldeuterium oxide revealed that the equatorial H-2 proton was most rapidly exchanged, followed by the sterically identical H-1
and H-3 protons, which exchanged at a significantly slower rate.