848900-41-4

Upstream product

• 920267-56-7 4-methylphenyl 1-thio-β-D-galactofuranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 90244-45-4 methyl 2,3,5,6-tetra-O-acetyl-α/β-D-galactofuranoside 
• 106-45-6 para-thiocresol 

Downstream Products

• 848900-39-0 p-tolyl 2,3-anhydro-5,6-O-isopropylidene-1-thio-β-D-gulofuranoside 
• 1359987-91-9 methyl 2-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside 
• 1359987-92-0 methyl 2-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside 
• 1359987-94-2 methyl 2-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 1359987-84-0 p-tolyl 3-O-benzoyl-5,6-O-isopropylidene-1-thio-β-D-galactofuranoside 
• 1359987-83-9 p-tolyl 2-O-benzoyl-5,6-O-isopropylidene-1-thio-β-D-galactofuranoside 
• 1374633-02-9 (2S,3S,4R,5S)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(p-tolylthio)tetrahydrofuran-3-yl 4-oxopentanoate 
• 1374633-03-0 (2S,3R,4R,5S)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-5-(p-tolylthio)tetrahydrofuran-3-yl 4-oxopentanoate 
• 1374633-04-1 (2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate 
• 1374632-99-1 (2R,3S,4R,5S)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(p-tolylthio)tetrahydrofuran-3-ol 
• 1374633-00-7 (2S,3R,4R,5S)-4-(tert-butyldiphenylsilyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(p-tolylthio)tetrahydrofuran-3-ol 
• 1033560-31-4 4-methylphenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside 
• 1612138-69-8 (2S,3S,4R,5S)-2-((2S,3S,4R,5R)-4-(benzoyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yloxy)-5-((R)-1,2-bis(benzoyloxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate 
• 1612138-71-2 (2R,3S,4R,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yl benzoate 

Relevant academic research and scientific papers

Total synthesis of fuzinoside

The first total syntheses of fuzinoside (1b) were achieved from d-galactose through two strategies (BCA and ABC) in 11 (total yield: 5.0%) and 15 (total yield: 3.7%) steps, respectively. Comparison of NMR data of synthetic compound 1b and those of the fuzinoside isolated from the lateral roots of Aconitum carmicaelii suggests that the structure reported in the literature1,2 might not be accurate. The synthetic fuzinoside (1b) exhibited moderate cardiac activity in the isolated bullfrog heart assay.

Synthesis of tetra- and hexasaccharide fragments corresponding to the O-antigenic polysaccharide of Klebsiella pneumoniae

The preparation of linear tetra- (1) and hexasaccharides (2), containing the repeating unit [→3)-β-Galf-(1→3)-α-Galp-(1→] present in the O-polysaccharide of the lipopolysaccharide of Klebsiella pneumoniae is described. The key step in their synthesis is the α-selective galactopyranosylation of 3-OH di- and tetrasaccharide acceptors (20 and 22) with a disaccharide trichloroacetimidate donor 19 in the presence of trimethylsilyl triflate in a diethyl ether-CH2Cl 2 mixture as solvent.

2,3-Anhydrosugars in glycoside bond synthesis. Application to α-D-galactofuranosides

We report here the use of 2,3-anhydro-D-gulofuranosyl thioglycosides and glycosyl sulfoxides in the synthesis of α-D-galactofuranosidic bonds, which are present in a range of bacterial and fungal glycoconjugates. This two-step method involves a stereosele