Convenient synthesis of 3-amino-3-deoxy-D-ribose
- 1 May 1968
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 46 (9) , 1586-1589
- https://doi.org/10.1139/v68-263
Abstract
3-Amino-3-deoxy-D-ribose and D-ribose were prepared from a derivative of D-xylose. 1,2-O-Isopropylidene-5-O-triphenylmethyl-α-D-xylofuranose (2) was oxidized by dimethyl sulfoxide – acetic anhydride to 1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-erythro-pentofuranos-3-ulose (3). The oxime (4) of this 3-keto sugar derivative was reduced with lithium aluminium hydride to 3-amino-3-deoxy-1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-ribofuranose (5), isolated as the acetamido derivative (6). Hydrolysis yielded 3-amino-3-deoxy-D-ribose hydrochloride. 3 was reduced by sodium borohydride to 1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-ribofuranose (7), which yielded D-ribose on hydrolysis.This publication has 5 references indexed in Scilit:
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