220340-02-3

Upstream product

• 220339-91-3 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole 
• 220339-89-9 1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-2-o-(p-toluenesulfoamidyl)phenylethyne 
• 65556-30-1 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues

The total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available α-methyl-D-mannoside in 10 steps including the following key steps: the C-glycosidation of a mannose derivative with a stannylacetylene, Castro indole synthesis, and Sc(ClO4)3-promoted coupling with L-serine-derived aziridine carboxylate. The glucose- and galactose-analogues of C-Man-Trp were also synthesized in a similar manner. Conformational analyses of the synthesized C-glycosyltryptophan and its synthetic intermediate are briefly discussed.