Abstract
The Claisen rearrangement of a spiro compound 1 derived from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, with triethyl orthopropionate afforded the rearrangement products 4, 5, and 6 as a 1:2.5:10 diastereomeric mixture. The reaction of 1 with trimethyl orthobutyrate provided a 1:3 mixture of 7 and 8. In both cases, the σ-bond formation proceeded predominantly from the β-side. This stereochemical outcome was opposite to that observed in the case of the rearrangement of 1 with triethyl orthoacetate.
| Original language | English |
|---|---|
| Pages (from-to) | 57-69 |
| Number of pages | 13 |
| Journal | Journal of Carbohydrate Chemistry |
| Volume | 20 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2001 Dec 1 |
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
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Takao, K. I., Saegusa, H., & Tadano, K. I. (2001). Orthoester Claisen rearrangement of a D-glucose-derived spirocyclic substrate. Journal of Carbohydrate Chemistry, 20(1), 57-69. https://doi.org/10.1081/CAR-100102543