FLUORINATED CYCLITOLS - AN IMPROVED SYNTHESIS OF 5-DEOXY-5-FLUORO-MYO-INOSITOL, ITS DEUTERIUM LABELING, AND SYNTHESIS OF A 5,5-GEM-DIFLUORO ANALOG

An improved synthesis of 5-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-neo-insolitol (I), followed by appropriate deprotection reactions. Reactions of DAST with the 5-keto...

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Bibliographic Details
Published inCarbohydrate research Vol. 207; no. 2; pp. 277 - 285
Main Authors JIANG, C, SCHEDLER, DJA, MORRIS, PE, ZAYED, AHA, BAKER, DC
Format Journal Article
LanguageEnglish
Published London Elsevier 25.10.1990
Subjects
Biochemistry & Molecular Biology
Chemistry
Chemistry, Applied
Chemistry, Organic
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
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Summary:An improved synthesis of 5-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-neo-insolitol (I), followed by appropriate deprotection reactions. Reactions of DAST with the 5-keto analogue of I gave the gem-difluoro compound, which upon deprotection afforded 5-deoxy-5,5-difluoro-myo-inositol. A 1H-n.m.r. study of the deuteration of 5-deoxy-5-fluoro-myo-inositol with Raney nickel-deuterium 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.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(90)84054-X