A Convenient, Gram-Scale Synthesis of 1-Deoxymannojirimycin

Abstract

A novel gram-scale synthesis of 1-deoxymannojirimycin from tetra-O-benzyl-d-glucopyranose in 9 steps and 28% overall yield with a limited number of purification steps is reported. The synthetic strategy is based on the regioselective deprotection and subsequent inversion of configuration of the OH group at C-2 in tetra-O-benzyl-d-glucono-δ-lactam, also an advanced intermediate toward the synthesis of 1-deoxynojirimycin derivatives.

Key words

iminosugars - glycosidase inhibitors - chiral pool - natural products - multi-step synthesis

• References

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