HCID 12836809, compound → HCID 86736778, compound

Participants

Reaction Steps

Treatment of 2.57 g; 10 mmoles of methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-arabino-hexopyranoside (III-A) in methylene dichloride with diazomethane/boron-trifluoride, as described in Example I gave the corresponding 4-O-methylderivative (III-B, 1.7 g., 63%): m.p. 185°; [α]D23° =-101° (c=1, in CHCl3); mass spectrum m/e 271 (H+); pmr spectrum (CDCl3); 1.31 (d, CH3 --C--5), 3.30 and 3.43 (two s, OCH3) and 4.70δ (broad s, C--1--H). Acid hydrolysis of compound III-B as in Example I (1.63 g., 6 mmoles) gave 2,3,6-trideoxy-4-O-methyl-3-trifluoroacetamido-L-arabino-hexopyranose (III-C, 1.51 g., 98%): m.p. 201°; [α]D23° =-12.7° (c=0.48, in CHCl3); mass spectrum m/e 257 (M+).

Provenance & Evidence