358620-68-5

Upstream product

• 220339-91-3 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole 
• 108-24-7 acetic anhydride 
• 65556-30-1 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 220339-86-6 8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-talo-oct-1-ynitol 
• 220339-89-9 1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-2-o-(p-toluenesulfoamidyl)phenylethyne 

Downstream Products

• 220339-97-9 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1H-3-formylindole 
• 358620-69-6 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester 
• 180509-18-6 α-C-Mannosyltryptophan 
• 849359-30-4 (Z)-3-[2-((2R,3R,4R,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-2-acetylamino-acrylic acid ethyl ester 

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.

Synthesis of a α-C-mannosyltryptophan derivative, naturally occurring C-glycosyl amino acid found in human ribonuclease 1

The title compound was synthesized from D-mannose, based on a novel C-glycosidation with tinacetylene, Castro-indole synthesis, and amino acid synthesis via dehydrotryptophan. Thieme.