1429413-18-2Relevant academic research and scientific papers
Asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1- deoxyallonojirimycin via a ring-expansion approach
Davies, Stephen G.,Figuccia, Aude L. A.,Fletcher, Ai M.,Roberts, Paul M.,Thomson, James E.
supporting information, p. 2042 - 2045 (2013/06/05)
The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.
