Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 5023-5026 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 40 |
| Issue number | 27 |
| DOIs | |
| Publication status | Published - 1999 Jul 2 |
Keywords
- Environmentally benign synthesis
- Glycosidation
- Montmofillonite K-10
- Olivose
- Olivoside
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Jyojima, T., Miyamoto, N., Ogawa, Y., Matsumura, S., & Toshima, K. (1999). Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst. Tetrahedron Letters, 40(27), 5023-5026. https://doi.org/10.1016/S0040-4039(99)00924-7