Chemo-enzymatic synthesis of five-membered azasugars as inhibitors of fucosidase and fucosyltransferase: An issue regarding the stereochemistry discrimination at transition states
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Reference (13)
- et al.
Tetrahedron Lett.
(1985)et al.J. Chem. Soc. Chem. Commun.
(1985)et al.Biochem. J.
(1990) - et al.
Glycobiology
(1992)bLook, G.C.; Fotsch, C.H.; Wong, C.-H. Acc. Chem. Res., in... - et al.
Adv. Enzymol.
(1987)Chem. Res.
(1990) - et al.
J. Am. Chem. Soc.
(1990)et al.Carbohydr. Res.
(1987)et al.J. Am. Chem. Soc.
(1991) - et al.
J. Org. Chem.
(1991)et al.J. Am. Chem. Soc.
(1991)et al.Bioorg. & Med. Chem. Lett.
(1992)
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2020, TetrahedronCitation Excerpt :In general, displacement of a triflate at C2 of a lactone by sodium azide in DMF can introduce nitrogen with either inversion or retention of configuration. Displacement of the 2-O-triflate in a γ-lactone in which all the ring substituents are cis gives a kinetic azide with a 2,3-trans relationship with the neighbouring oxygen; base catalysed isomerisation by azide gives the thermodynamically more stable azide in which all the substituents on the lactone ring are cis [9]. The epimeric azides are always very different in polarity and easily separated by flash chromatography [10].
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