Abstract
The O,O-dibenzyl-S-glycosyl phosphothioite derived from 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-glucopyranose rearranges under the influence of triethylborane and air to provide the corresponding 1-C-pyranosyl-O,O-dibenzylphosphonothioate, a new type of carbohydrate derivative. The isomeric beta phosphothioite is compared, and evidence of a radical chain mechanism for the Pudovik rearrangement is presented.
Original language | English (US) |
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Pages (from-to) | 1945-1949 |
Number of pages | 5 |
Journal | Tetrahedron Letters |
Volume | 48 |
Issue number | 11 |
DOIs | |
State | Published - Mar 12 2007 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry