Novel stereocontrolled glycosidations of 3,4-di-O-protected olivoses and alcohols using a heterogeneous and environmentally benign solid acid, montmorillonite K-10, have been developed. The glycosidations of the 3-O-Ac- 4-O-TBS-olivose (4) and various alcohols using montmorillonite K-10 in CH2CI2 at 25 °C exclusively gave the corresponding α-olivosides in high yields. On the other hand, the corresponding β-olivosides were predominately obtained by the glycosidations of the 3-O-TBS-4-O-Ac-olivose (5) and various alcohols under similar conditions.
- Environmentally benign synthesis
- Montmofillonite K-10
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry