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Details for article 5 of 178 found articles
| Title: |
A Convenient Synthesis of 3-Deoxy-D-gluco-2-octulosonate (D-gluco-KDO) |
| Author: |
Lafont, Dominique Hoch, Monika Schmidt, Richard R. |
| Appeared in: |
Journal of carbohydrate chemistry |
| Paging: | Volume 5 (1986) nr. 4 pages 601-614 |
| Year: |
1986-12-01 |
| Contents: |
β-Lithiated acrylates have proven to be versatile pyruvate β-carbanion equivalents which are also useful in D-manno-KDO synthesis. The secondary amine adducts of acetylenedicarboxylate 4 display the same versatility, as demonstrated in this paper. However, on reaction with 2,3:4, 5-di-O-isopropylidene-D-arabinose 6, the diastereofacial selectivity is in favor of the gluco-isomer, thus leading with lithiated compounds 4A, preferentially to α-aminobutenolides 7-(g). The best results were obtained with the morpholine adduct of di-tert.-butyl acetylenedicarboxylate 4d which afforded the gluco-isomer 7d-(g) as an easily separable crystalline material. Its deamination and concomitant deisopropylidenation with trifluoroacetic acid provided the known α-hydroxy-butenolide 8b-(g), which was transformed via decarboxylation product 9-(g) to D-gluco-KDO 10-(g) thus concluding a convert four step synthesis of this compound via crystalline intermediates. |
| Publisher: |
Taylor & Francis |
| Source file: |
Elektronische Wetenschappelijke Tijdschriften |
Details for article 5 of 178 found articles
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