849359-35-9

Upstream product

• 287962-77-0 (2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyl-tetrahydropyran 
• 443915-85-3 trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane 
• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 849359-24-6 1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-o-(p-toluenesulfoamidyl)phenylethyne 
• 849359-27-9 2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-(p-toluenesulfonyl)indole 
• 849359-29-1 2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1H-indole 
• 104597-98-0 (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine 

Downstream Products

• 849359-37-1 2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan 

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.