161602-55-7

Upstream product

• 124477-00-5 phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 108-98-5 thiophenol 
• 120095-47-8 phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 600-22-6 pyruvic acid methyl ester 
• 152488-27-2 phenyl 2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside 

Downstream Products

• 195316-83-7 (2R,3aS,4R,6R,7R,7aS)-7-Benzoyloxy-4-benzoyloxymethyl-2-methyl-6-((2R,3S,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-carboxylic acid methyl ester 
• 195316-86-0 (2R,3aS,4R,6R,7R,7aS)-7-Benzoyloxy-4-benzoyloxymethyl-2-methyl-6-((2R,3S,4S,5R,6S)-3,4,5-tris-benzoyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-carboxylic acid methyl ester 
• 195317-02-3 (2R,3aS,4R,6R,7R,7aS)-7-Benzoyloxy-4-benzoyloxymethyl-2-methyl-6-((2R,3S,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-bromo-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Studies towards the total synthesis of repeating unit of O-sulfated polysaccharide from marine bacterium Cobetia pacifica KMM 3878

Herein we report assembly of the appropriately protected trisaccharide repeating unit of Cobetia pacifica KMM 3878 O-sulfated polysaccharide. Our synthesis involves 3,4-O-pyruvilated galactose as the key building block which acts as a donor as well as acceptor in the construction of trisaccharide. We obtained the R isomer as a major stereoisomer in the pyruvilation reaction. The glycosylations proceeded with high stereo and regioselectivity.

Preparation of Diastereomeric 3,4-O-Pyruvate Acetal-Containing D-Galactopyranose Derivatives, Structural Assignment and Use for Oligosaccharide Synthesis

Treatment of phenyl 1-thio- and allyl 2,6-di-O-benzoyl-D-galactopyranosides 3 with methyl pyruvate and BF3*Et2O in various solvents gave 1,6-anhydro-3,4-di-O-benzoyl-2-deoxy-2-phenylthio-β-D-idopyranose (4) and the corresponding diastereomers of 3,4-O-pyruvate acetal-containing galactosides 5.The phenyl 1-thio-β-galactoside R-5a and the allyl α-galactoside R-5b were both converted into methyl 3,4-O--β-D-galactopyranoside (9), the structure of which as well as that of 4 was confirmed by X-ray crystallography.Compound R-5a was converted into 5-pentyl 6-O-benzoyl-3,4-O--β-D-galactopyranoside (18) by using the (2-chloroacetoxymethyl)benzoyl (CAMB) group for the temporary protection of position 2.Glucosamination of 18 and subsequent deblocking of the intermediate disaccharide gave β-D-GlcpNAc-(1-->2)-3,4-(S)-pyruvate-β-D-Galp-O(CH2)5NH2 (21) which represents a fragment of the Escherichia coli K 47 polysaccharide. - Key Words: Galactosides, 3,4-pyruvylated / Oligosaccharides / Carbohydrates / Escherichia coli