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| Titel: |
Protecting Group Manipulation on d-Glucosamine Propane-1,3-diyl Dithioacetal |
| Auteur: |
Chen, Yue-Lei Leguijt, Robin Redlich, Hartmut |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 26 (2007) nr. 5-6 pagina's 279-303 |
| Jaar: |
2007-07 |
| Inhoud: |
d-glucosamine propane-1,3-diyl dithioacetal is a versatile synthetic building block, especially when being incorporated with the Corey-Seebach method. Hence, exploring compatible protecting group patterns on this compound mainly for use with the Corey-Seebach method is a fundamental work. Various protecting group strategies were applied. Typically, N-protection of d-glucosamine propane-1,3-diyl dithioacetal yielded N-phthaloyl, N-Boc, and N-Ac derivatives. On the N-Ac derivative, experiments differentiating 3,4- and 5,6-hydroxyls by basic stable protecting groups yielded useful intermediates. Selective protections of the 6-hydroxyl of the N-Ac derivative were also applied. The remaining secondary hydroxyls of the resulting N-Ac-6-O-acyl d-glucosamine propane-1,3-diyl dithioacetals could be methoxymethylated to tri-O-MOM derivatives or protected by a unique one-pot discriminating protection to form the N-acyl-6-O-acyl- 3,4-O-methylene-5-O-methoxymethyl d-glucosamine propane-1,3-diyl dithioacetals as useful intermediates. |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
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