Abstract
2,3-O-isopropylidene-D(+)-glyceraldehyde reacts with di- l-menthyl-malonate to give the penturonates 2a, and 3a in an erythro- threo 8.5:1 ratio. The C 2-branched sugars 2-deoxy-2-hydroxymethyl-3,4- erythro-pentitol 6 and 2-deoxy-2-hydroxymethyl-3,4- threo-pentitol 7 were obtained by submitting 2a and 3a to routine procedures. The same reaction, performed with di- d-menthylmalonate, resulted in a decreased diastereoselectivity, providing a 2.5:1 mixture of erythro and threo diastereomers.
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