262601-77-4Relevant articles and documents
Stereocontrolled introduction of an amino group at C-6 of D-galactose via (3,3)-sigmatropic rearrangements - Novel synthesis of lincosamine and 7- epi-lincosamine precursors
Gonda, Jozef,Zavacká, Eva,Bude?ínsky, Miloslav,Císarová, Ivana,Podlaha, Jaroslav
, p. 525 - 529 (2000)
A new and stereoselective route to the aminoglycoside components of the antibiotics lincomycin and clindamycin is presented. The key step involves diastereoselective introduction of the amino group at C-6 of D-galactose by (3,3)-sigmatropic rearrangements of the corresponding allylic (Z)- trifluoroacetimidate and (Z)- and (E)-allylic thiocyanates. Epoxidation of the resulting trifluoroacetamide with m-CPBA led to the epoxide with high threo-selectivity.