Synthesis of the Antibiotic 1,5-dideoxy-1,5-imino-d-mannitol |
| |
| Authors: | H. J. G. Broxterman J. J. Neefjes G. A. Van der Marel H. L. Ploegh J. H. Van Boom |
| |
| Affiliation: | 1. Gorlaeus Laboratory , P. O. Box 9502, 2300, RA Leiden, The Netherlands;2. Antoni van Leeuwenhoekhuis , Plesmanlaan 121, 1066, CX, Amsterdam, The Netherlands |
| |
| Abstract: | Abstract Easily accessible benzyl 2,3-O-isopropylidene-α-D-mannofuranoside (1) was converted in six steps into benzyl 2,3-O-isopropylidene-5-N-benzyl-5-deoxy-6-O-benzyl-α-D-mannofuranoside or benzyl 2,3-O-isopropylidene-5-azido-5-deoxy-6-O-benzyl-α-D-mannofuranoside. Both compounds afforded, after hydrogenolysis and acidolysis, 1-deoxymannojirimycin in an overall yield of 38% based on 1. |
| |
| Keywords: | |
|
|
