Synthesis of higher carbon sugars from dihydroxyacetone and d-arabinose: an organocatalytic approach |
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| Authors: | Maciej Cieplak Magdalena Ceborska Piotr Cmoch Sławomir Jarosz |
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| Affiliation: | 1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44, 01-224 Warszawa, Poland;2. Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka, 44, 01-224 Warszawa, Poland |
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| Abstract: | The reaction of 2,3:4,5-diacetone-d-arabinose with protected dihydroxyacetone catalyzed by l-proline afforded two diastereoisomeric octoses in a 7:1 ratio in 75% yield. The anti (3S,4S) configuration at the newly created stereogenic centers was assigned to the main isomer on the basis of the X-ray analysis. The same reaction when catalyzed with unnatural d-proline provided the same products in a 1:20 ratio. |
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