Asymmetric dihydroxylation of d-glucose derived alpha,beta-unsaturated ester: synthesis of azepane and nojirimycin analogues.
The asymmetric dihydroxylation of a d-glucose derived alpha,beta-unsaturated ester 3 afforded syn vicinal diols in good to high diastereoselectivity. The conversion of these vicinal diols to the corresponding cyclic sulfate, regio-, stereoselective nucleophilic ring opening by sodium azide, and LAH reduction afforded amino heptitols 7a,b that were converted to azepane 1c,d and nojirimycin analogues 2c,d.
Dhavale
Dilip D
DD
Department of Chemistry, Garware Research Centre, University of Pune, Pune-411 007, India. ddd@chem.unipune.ernet.in
Markad
Shankar D
SD
Karanjule
Narayan S
NS
PrakashaReddy
J
J
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D001381:Azepines / Q000138:chemical synthesis*; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D006900:Hydroxylation; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D001381:Azepines; D004952:Esters; D007202:Indicators and Reagents; D017485:1-Deoxynojirimycin; D005947:Glucose; D005944:Glucosamine; C013626:nojirimycin