Diastereoselective synthesis of glycosylated prolines as alpha-glucosidase inhibitors and organocatalyst in asymmetric aldol reaction.
1,3-Dipolar cycloaddition of azomethine ylides and glycosyl E-olefins in presence of LDA led to diastereoselective formation of C-glycosylated proline esters. The selected esters on regioselective hydrolysis with LiOH gave C-glycosyl prolines. Few of the proline esters exhibited very good alpha-glucosidase inhibitory activity. The organocatalytic activity of the proline derivatives in a prototype Aldol reaction has also been investigated.
Pandey
Jyoti
J
Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226001, India.
Dwivedi
Namrata
N
Singh
Nimisha
N
Srivastava
A K
AK
Tamarkar
A
A
Tripathi
R P
RP
D000447:Aldehydes; D002384:Catalysis; D065089:Glycoside Hydrolase Inhibitors; D006031:Glycosylation; D011392:Proline / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000447:Aldehydes; D065089:Glycoside Hydrolase Inhibitors; C116609:3-hydroxybutanal; D011392:Proline