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| Titel: |
High-Pressure Approach to the Synthesis of Optically Pure Methyl 4-Deoxyheptosides |
| Auteur: |
Jurczak, Janusz Bauer, Tomasz Kihlberg, Jan |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 4 (1985) nr. 3 pagina's 447-450 |
| Jaar: |
1985-09-01 |
| Inhoud: |
Recently we have described1 high pressure (4+2) cycloaddition of l-methoxybuta-1,3-diene (1)to 2,3-0-isopropylidene-D-glyceraldehyde (z), which gives rise to chiral cycloadducts 3 (Scheme). action was carried out under high-pressure conditions (22 kbar, 50°C. diethyl ether as solvent, 20 h, 80% yield)2 four diastereoisomeric adducts were formed in a ratio of 3a:3b:3c:3d=66:16:13:5. The reaction mixture was separated by column chromatography yielding two fractions which contained diastereoisomeric mixtures (3a+3b) and (3c+3d), respectively. Absolute configuration at the C-5 carbon atom in both mixtures was established by chemical correlation.' These results prompted us to use a mixture (3a+3b), being stereochemically pure at C-5 chiral center, in the synthesis of optically active methyl 4-deoxyheptosides (Scheme). |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 89 van 252 gevonden artikelen
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