Monomer Synthesis

Introduction

Several strategies for monomer synthesis have been successfully utilised to generate both five- and six-membered ring glycals.

Six-membered ring glycals

A Diels-Alder approach using Danishefsky's diene 1.¹

Approaches from peracetyl analogues of D-galactose (2), D-glucose and D-xylose.²

Five-membered ring glycals

Monomers from thymidine (3).³

Vinylepoxide and vinylaziridine rearrangements.⁴

Modest enantioselectivity is obtained in the chiral auxiliary tethered vinyl epoxide rearrangements.

References

1. Danishefsky S., Kerwin Jr. J.F. and Kobayashi S., J. Am. Chem. Soc., 1982, 104, 783.
2. Kozikowski A.P., Lee J., J. Org. Chem., 1990, 55, 863.
3. Larsen E., Jørgensen P.T., Sofan M.A. and Pedersen E.B., Synthesis, 1994, 1037.
4. Batsanov A.S., Byerley A.L.J., Howard J.A.K. and Steel P.G., Synlett.1996, 411.