Concepedia

A Short and Practical Synthesis of 1-Deoxynojirimycin

James R. Behling, P. FARID, John R. Medich, Mike G. Scaros, Michael L. Prunier, Richard M. Weier, Ish Khanna

Synthetic Communications · 1991 · 29 citations · 5 references

DOI

Abstract

Abstract The potent glucosidase inhibitor 1-deoxynojirimycin was synthesized from L-sorbose using a short synthesis and only one protecting group. The last step, which constituted the removal of an acetonide protecting group and an intramolecular reductive amination, was accomplished on an acidic lon-exchange resin. This provided a synthesis capable of being operated on a multi-kilogram scale.

References

5

Enzyme‐Catalyzed Synthesis of 1‐Deoxymannojirimycin, 1‐Deoxynojirimycin, and 1,4‐Dideoxy‐1,4‐imino‐<scp>D</scp>‐arabinitol

Thomas Ziegler, Alexander Straub, Franz Effenberger · Angewandte Chemie International Edition in English · 1988 · 139 citations

, , +13

Inhibition of mammalian digestive disaccharidases by polyhydroxy alkaloids

A. M. Scofield, Linda E. Fellows, Robert J. Nash et al. · Life Sciences · 1986 · 136 citations

, , +2

Synthesis of deoxymannojirimycin fagomine deoxynojirimycin 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol 2-acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol 2S,3R,4R,5R-trihydroxypipecolic acid and 2S,3R,4R,5S-trihydroxypipecolic acid from methyl 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside

George W. J. Fleet, Linda E. Fellows, Paul W. Smith · Tetrahedron · 1987 · 104 citations

, , +9

Isolation and characterization of a new trehalase inhibitor, S-GI.

Sawao Murao, Shigekazu Miyata · Agricultural and Biological Chemistry · 1980 · 93 citations · Full text

, , +6

Synthesis of l-fructose

Chyi-Cheng Chen, Roy L. Whistler · Carbohydrate Research · 1988 · 43 citations

, , +4