Scalable Synthesis of a Mycosamine Donor. Overcoming Difficult Reactivity in Allose Systems

Abstract

Mycosamine is a dideoxyaminosugar found in medicinally relevant macrolides, including amphotericin B and nystatin. Herein we report a reliable, high yielding, scalable synthesis of a mycosamine donor. A major goal of our approach was to minimize purifications via judicious selection of protecting groups; the inherent properties of the allose framework created some deprotection obstacles that were ultimately solved.

Key words

asymmetric synthesis - natural products - glycosylations - protecting groups - medicinal chemistry

References

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