Kozikowski A. P., . Tetrahedron Letters, 1989, 30(26), 3365-3368.et al
Customer Inquiry:
An expert in chiral drug manufacturing reached out to Alfa Chemistry to find a dependable fluorination agent for conducting stereoselective hydroxyl group substitution with fluorine atoms. The team used a gentle yet effective approach to create (-)-fluoromyosinol, which serves as an essential intermediate in their drug development.
Solution Provided:
Alfa Chemistry recommended diethylamino sulfur trifluoride (DAST, Catalog OFC38078090-1) for fluorination. The research by Kozikowski et al. serves as our reference point. Kozikowski and his team demonstrated how (+)-fluoroinositol could be synthesized from betulinol through a two-step process using DAST. The reaction proceeds through a DAST intermediate formation that promotes hydroxyl dissociation, enabling efficient nucleophilic substitution by fluoride and stereochemical inversion.
Results:
The client used Alfa Chemistry's DAST for synthesis while maintaining low reaction temperatures to avoid decomposition. The chemical reaction produced high yields and precise stereochemical outcomes that satisfied strict purity standards.
Kuroboshi M., et al. Tetrahedron Lett., 1991, 32, 1215.
