Chloroform → HCID 86738947, compound

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Reaction Steps

Stereoselective reduction of 0.5 g of the intermediate VIII (prepared as described in Example 1) in 40 ml of methanol in the presence of 0.5 g of 20% palladium on charcoal under a pressure of 20 atmospheres gave, in quantitative yield, methyl 2,3,4,6-tetradeoxy-4-C-methyl-3-trifluoroacetamido-L-arabino-hexopyranoside (XI) as a white solid: m.p. 132°-134° C., [α]D23° -82° (c=0.5, CHCl3). The PMR spectrum (CDCl3) showed absorptions at: 0.90 (d, CH3 --C--4), 1.23 (d, CH3 --C--5), 1.26 (m, H--C--4), 3.42 (s, OCH3), 3.70 (dq, H--C--5), 4.20 (m, H--C--3) and 4.87 δ (dd, H--C--1). A solution of 0.385 g, 1.5 mmol of XI in 7 ml of acetic acid and 28 ml of water was heated at 100° C. for two hours and then evaporated to dryness to give, in quantitative yield, 2,3,4,6-tetradeoxy-4-C-methyl-3-trifluoroacetamido-α-L-arabino-hexopyranose (XII) as a white solid: m.p. 158°-159° C., [α]D23° -62° (c=0.5, CHCl3).

Provenance & Evidence