79258-27-8

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 79299-18-6 methyl 3,4-O-(2-nitrobenzylidene)-α-L-fucopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 79258-26-7 methyl 4-O-(2-nitrobenzoyl)-2-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-L-fucopyranoside 
• 86734-77-2 methyl 3-O-(2-nitrobenzoyl)-2-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-L-fucopyranoside 
• 86734-74-9 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R,5S,6S)-4,5-dihydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 552-89-6 2-nitro-benzaldehyde 
• 86734-76-1 methyl 4-O-(2-nitrobenzoyl)-2-O-(tetra-O-acetyl-β-D-galactopyranosyl)-α-L-fucopyranoside 
• 86734-77-2 methyl 3-O-(2-nitrobenzoyl)-2-O-(tetra-O-acetyl-β-D-galactopyranosyl)-α-L-fucopyranoside 
• 79258-25-6 methyl 4-O-(2-nitrobenzoyl)-2,3-di-O-(tetra-O-acetyl-β-D-galactopyranosyl)-α-L-fucopyranoside 
• 79258-25-6 methyl 4-O-(2-nitrobenzoyl)-2,3-di-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-L-fucopyranoside 

Relevant academic research and scientific papers

The Photochemistry of Carbohydrate Derivatives. Part 5. Synthesis of Methyl 2,3-Di-O-(β-D-glucopyranosyl)-α-L-fucopyranoside and Methyl 2,3-Di-O-(β-D-galactopyranosyl)-α-L-fucopyranoside using Photolabile O-(2-Nitrobenzylidene) Acetals as Temporary Blocking Groups

The branched trisaccharide derivatives (6) and (12) named in the title have been synthesised from methyl 3,4-O-(2-nitrobenzylidene)-α-L-fucopyranoside (1) using the 2-nitrobenzylidene residue as a temporary blocking group.Glucosylation and galactosylation of compound (1) afforded the blocked disaccharides (2) and (7), respectively, and upon sequential photolysis and oxidation these were regioselectively transformed into the partially blocked 4-O-(2-nitrobenzoyl)disaccharides (4) and (9), the 3-O-(2-nitrobenzoyl) positional isomers being formed in 5 and 3percent yield, respectively.Further glycosylation of compounds (4) and (9) gave the fully protected trisaccharide derivatives (5) and (11), respectively, which were converted into the title compounds (6) and (12) upon deacylation.

Synthesis of some Branched Trisaccharides using Photolabile o-Nitrobenzylidene Acetals as Temporary Protecting Groups

Methyl 2-O-(β-D-glucopyranosyl)-3-O-(β-D-glucopyranosyl)-α-L-fucopyranoside (4), methyl 2-O-(β-D-galactopyranosyl)-3-O-(β-D-galactopyranosyl)-α-L-fucopyranoside (5), and methyl 3-O-(β-D-glucopyranosyl)-4-O-(β-D-glucopyranosyl)-α-L-rhamnopyranoside (9) have been synthesized using o-nitrobenzylidene acetals as photosensitive temporary protecting groups.