A convenient synthetic route to 2-deoxy-l-ribose and 2-deoxy-d-xylose☆

Add time:08/16/2019    Source:sciencedirect.com

2-Deoxy-l-ribose (2-deoxy-l-erythro-pentose) and 2-deoxy-d-xylose (2-deoxy-d-threo-pentose) were synthesized from 2-deoxy-d-galactose (2-deoxy-d-lyxo-hexose) and 2-deoxy-d-glucose (2-deoxy-d-arabino-hexose), respectively. Conversion of the 2-deoxy-d-hexoses to the methyl 2-deoxy-d-hexofuranosides, followed by periodate oxidation, reduction with borohydride, and mild acid hydrolysis, gave 2-deoxy-l-ribose and 2-deoxy-d-xylose in 55 and 44% yield, respectively. 2-Deoxy-l-ribose was identified by paper chromatography, GLC, and as its “anilide.” 2-Deoxy-d-xylose was identified by paper chromatography. This procedure provides a rapid and convenient method for obtaining these unusual sugars, and may be extended to the synthesis of other 2-deoxy-pentoses.

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