3-Deoxy-d-threopentofuranose 5-phosphate, a substrate of arabinose 5-phosphate isomerase, has been synthesised starting from d-arabinose. Selective protection of the hydroxyl groups at C-1, C-2, and C-5 allowed deoxygenation of position 3 by conversion into a thiocarbamate and radical reduction. Deprotection and phosphorylation of the primary hydroxyl group and final deprotection of the other hydroxyl groups afforded the desired compound.
Airoldi, C., Merlo, S., Nicotra, F. (2010). Synthesis of 3-Deoxy-D-threopentofuranose 5-Phosphate, a Substrate of Arabinose 5-Phosphate Isomerase. JOURNAL OF CARBOHYDRATE CHEMISTRY, 29(1), 30-38 [10.1080/07328300903477812].
Synthesis of 3-Deoxy-D-threopentofuranose 5-Phosphate, a Substrate of Arabinose 5-Phosphate Isomerase
AIROLDI, CRISTINA;NICOTRA, FRANCESCO
2010
Abstract
3-Deoxy-d-threopentofuranose 5-phosphate, a substrate of arabinose 5-phosphate isomerase, has been synthesised starting from d-arabinose. Selective protection of the hydroxyl groups at C-1, C-2, and C-5 allowed deoxygenation of position 3 by conversion into a thiocarbamate and radical reduction. Deprotection and phosphorylation of the primary hydroxyl group and final deprotection of the other hydroxyl groups afforded the desired compound.
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