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.
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