期刊
TETRAHEDRON
卷 76, 期 I, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.130758
关键词
Iminosugars; Sugar mimics; Rhamnosidase inhibitors; Glucosidase inhibitors; Deoxysugars; Pyrrolidine synthesis; Benzylidene acetals; Hanessian Hullar reaction
资金
- Japanese Society for the Promotion of Science (JSPS KAKENHI) [JP17K08362]
- Biotechnology and Biological Sciences Research Council [BB/M011321/1]
- University of Kagawa
- Xunta de Galicia (Centro Singular de Investigacion de Galicia) [ED431B 2018/13, CN2011/037, GRC2014/040]
- European Union (European Regional Development Fund-ERDF)
- BBSRC [BB/M011321/1] Funding Source: UKRI
The key step in the syntheses of highly substituted trans-3,4-dihydroxypyrrolidines is introduction of bromide by stereospecific and regiospecific Hanessian-Hullar reactions; benzylidene lactones of L-rhamnonolactone and 6-deoxy-this should be small unnpercase D not L why can I not correct this-gulonolactone allow introduction of N at C2 with inversion or retention of configuration. Initially a protecting group, the benzylidene acetal then provides a bromide at C5 to allow formation of the pyrrolidine ring. With silyl protecting groups, bromide was introduced at C5 with inversion of configuration whereas benzoyl protection gave a mixture of retention and inversion, indicative of neighbouring group participation in a Hanessian-Hullar reaction. Four stereoisomeric pyrrolidines - iminosugar mimics of sand beta-L-rhamnulose and alpha- and beta-6-deoxy-D-sorbose were prepared. Only the alpha-L-rhamnulose mimic showed moderate inhibition of rhamnosidase but some were good inhibitors of alpha-glucosidases; none inhibited rhamnose isomerase and they had a small effect as synthetic inducers of the rhamnose catabolic operon in E. coli. (C) 2019 Elsevier Ltd. All rights reserved.
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