168138-11-2

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 83-87-4 D-Mannose pentaacetate 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 19493-09-5 Methylenetriphenylphosphorane 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 159353-70-5 phenyl 2-O-p-methoxybenzyl-3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside 
• 159407-19-9 phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 158716-07-5 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 168138-20-3 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane 
• 168138-21-4 (1'R,2R,2'R,4R,5S)-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-5-hydroxy-2-phenyl-1,3-dioxane 
• 168254-34-0 (1'R,2R,2'R,4R,5S)-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-5-hydroxy-2-phenyl-1,3-dioxane 
• 172967-72-5 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane 
• 168138-13-4 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-hydroxy-3-butenyl>-2-phenyl-1,3-dioxane 
• 168138-12-3 (2R,4S)-4-[(1R,2R)-1-Benzyloxy-2-(4-methoxy-benzyloxy)-but-3-enyl]-2-phenyl-[1,3]dioxan-5-one 

Relevant academic research and scientific papers

Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: Sugar moiety of antitumor antibiotic bleomycin

A new route to the disaccharide moiety (2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose) of the antitumor agent bleomycin was developed. Both the L-gulose synthon 21 and the 3-O-carbamoyl-D-mannose segment 30 were prepared from D-mannose in a regioselective manner by applying stannylene acetal methodology. Glycosylation of 21 with 30 proceeded smoothly, and further conversion to disaccharide derivatives (33 and 34) was successfully accomplished.

Preparation of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: Synthetic study on the sugar moiety of antitumor antibiotic bleomycin

A new practical route to the disaccharide moiety of bleomycin was developed. Both of key building blocks 9 and 16 were prepared from D-mannose in a regioselective manner by applying stannylene acetal methodology. Glycosylation of the allyl alcohol 9 with the trichloroacetimidate 16 proceeded smoothly, and the further incorporation to the disaccharide moiety was succesfully accomplished.