Abstract
The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 1641-1650 |
| Number of pages | 10 |
| Journal | Carbohydrate Research |
| Volume | 338 |
| Issue number | 16 |
| DOIs | |
| Publication status | Published - Jul 29 2003 |
Keywords
- Deoxygenation
- Phospho sugar
- α-Hydroxyphosphonate
ASJC Scopus subject areas
- Analytical Chemistry
- Biochemistry
- Organic Chemistry
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Cite this
Hanaya, T., Sugiyama, K. I., Kawamoto, H., & Yamamoto, H. (2003). Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates). Carbohydrate Research, 338(16), 1641-1650. https://doi.org/10.1016/S0008-6215(03)00235-0