Synthesis of the 2-deoxy trisaccharide glycal of antitumor antibiotics landomycins A and E

• Concise synthesis of the 2-deoxy trisaccharide glycal has been accomplished.
• Stereoselective construction of 2-deoxy β-disaccharide is achieved via anomeric O-alkylation.
• A concomitant debenzylation and elimination strategy is utilized for the synthesis of glycal.

Synthesis of the 2-deoxy trisaccharide glycal of antitumor antibiotics landomycins A and E has been described. The synthesis involves an anomeric O-alkylation for the synthesis of 2-deoxy β-linked disaccharide, a tert-butyldimethylsilyl triflate-catalyzed α-selective L-rhodinosylation, and a lithium 4,4′-di-tert-butylbiphenyl-mediated reductive debenzylation and concomitant reductive lithiation-elimination for the production of the 2-deoxy trisaccharide glycal.

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