Abstract
An efficient divergent synthesis of L-sugars and L-iminosugars from D-sugars is described. The important intermediate. δ-hydroxyalkoxamate. prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxime compound and the N-cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O-/N-cyclization of the δ-hydroxyalkoxamate. Suitable protection at the 6-position of δ-hydroxyalkoxamate. derived from D-glucono-1,5-lactone, afforded the corresponding O-alkylation product alone. Thus we succeeded in applying this to the total synthesis of L-iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of δ-glucono/galactono-1,5-lactone into the corresponding L-iminosugars (L-idonolactam and L-altronolactam) was achieved.
Original language | English |
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Pages (from-to) | 5868-5877 |
Number of pages | 10 |
Journal | Chemistry - A European Journal |
Volume | 12 |
Issue number | 22 |
DOIs | |
Publication status | Published - Jul 24 2006 |
Externally published | Yes |
Keywords
- Azasugars
- Carbohy-drates
- Lactams
- Lactones
- Mitsunobu reaction
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry