Novel synthesis of the glycosidase inhibitor deoxymannojirimycin and of a synthetic precursor D-lyxo-hexos-5-ulose

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3353-3356

  O'Brien, Julie L ^a   Tosin, Manuela ^a   Murphy, Paul V ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYNOJIRIMYCIN; 5 KETOMANNOSE; 5-KETOMANNOSE; ANTIINFECTIVE AGENT; ANTIVIRUS AGENT; DRUG DERIVATIVE; ENZYME INHIBITOR; EPOXIDE; GLYCOSIDASE; MANNOSE; METHYL MANNOSIDE; METHYLMANNOSIDE;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

1-DEOXYNOJIRIMYCIN; ANTI-BACTERIAL AGENTS; ANTIVIRAL AGENTS; CHEMISTRY, PHARMACEUTICAL; ENZYME INHIBITORS; EPOXY COMPOUNDS; GLYCOSIDE HYDROLASES; MANNOSE; METHYLMANNOSIDES;

EID: 0035909646     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016596s     Document Type: Article

References (34)

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30. 4 conformation. Some epimerization of the α-azide (azide in equatorial orientation) to the β-azide can be observed during prolonged reaction times, which occur if more dilute concentrations of sodium methoxide are used. The epimerization can be avoided by reducing the reaction time by increasing methoxide concentration. See Supplementary information for details. It appears advantageous to use the pure α-azide in the final step rather than an α/β mixture as reduction of β-isomer (azide in axial orientation) is much slower.
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34. The yield is given after purification of 2 using chromatography; this requires further optimization as NMR indicates that the major product in the crude reaction mixture is 2, estimated to be 60%. We are also investigating the possibility of carrying out the final three steps in a single pot.