Efficient Synthesis of Orthogonally Protected Rare l-Hexoses and Derivatives

Abstract

Stereoselective preparations of protected rare sugars and derivatives, namely l-psicose, l-altritol, and l-talose have been achieved in 70, 44, and 18% yield, respectively, from an orthogonally protected l-glyceraldehyde derivative. The key step is the stereoselective proline-catalyzed aldol reaction of this aldehyde with dioxanone.

Key words

organocatalysis - aldol reaction - rare sugars - orthogonal protection - L-psicose - L-talitol - L-altritol - L-talose

• References

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