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Details van artikel 163 van 252 gevonden artikelen
| Titel: |
Synthesis and Conformation of Substituted 2,6-Dioxabiocyclo[3.1.1]heptanes: 1, 3-Anhydro-2, 4-di-O-benzyl-β-D-fucopyranose |
| Auteur: |
Yang, Cuijian Cao, Lingxiao Kong, Fanzuo |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 11 (1992) nr. 3 pagina's 379-395 |
| Jaar: |
1992-04-01 |
| Inhoud: |
The title 1,3-anhydro sugar (9) was synthesized from methyl α-D-fucopyranoside in 7 steps, most of which were carried out readily in high yield. The key intermediate for the synthesis was 3-O-acetyl-2,4-di-O-benzyl-α-D-fucopyranosyl chloride (7), which was transformable into the target compound by ring closure with potassium tert-butoxide. Calculations using the modified Karplus equation for vicinal coupling constants of compound 9 suggested that the conformation of the 1,3-anhydro sugar ether is essentially B2 5 with some flattening of the boat head at C-5 for the pyraranose ring. The 1,3-dioxane ring is in a chair conformation. The conformation of 9 was confirmed by empirical force-field calculations (MMP2). Conformational analysis with the MMP2 program for 1,3-anhydro-2,4-di-O-benzyl-6-deoxy-β-D-glucopyranose (13) and 1,3-anhydro-2,4-di-O-benzyl-β-D-rhamnopyranose (14) also showed good agreement with the results obtained by 1H NMR spectrometry. |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 163 van 252 gevonden artikelen
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