Aldol reaction of beta-C-glycosylic ketones: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides.
A series of beta-C-glycosylic ketones were prepared starting from d-glucose, d-xylose, d-mannose, and cellobiose. The beta-C-glycosylic ketones on aldol condensation with different aromatic aldehydes in the presence of a suitable organocatalyst led to the formation of respective C-(E)-cinnamoyl glycosides stereoselectively in good yields as precursors for the synthesis of biologically active compounds.
Bisht
Surendra Singh
SS
Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, India.
Pandey
Jyoti
J
Sharma
Anindra
A
Tripathi
Rama Pati
RP
D002475:Cellobiose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D007659:Ketones / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014994:Xylose / Q000737:chemistry
D006027:Glycosides; D007659:Ketones; D002475:Cellobiose; D014994:Xylose; D005947:Glucose; D008358:Mannose