124477-00-5

Upstream product

• 108-98-5 thiophenol 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 270075-72-4 phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 124476-99-9 phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 

Downstream Products

• 478244-99-4 C₃₀H₃₀O₉ 
• 124477-11-8 1,5-anhydro-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-D-lyxo-hex-1-enitol 
• 124476-98-8 phenyl 3,4-O-isopropylidene-2,6-di-O-methyl-1-thio-β-D-galactopyranoside 
• 124477-04-9 3,4-O-isopropylidene-2,6-di-O-methyl-β-D-galactopyranosyl phenyl sulphone 
• 124476-99-9 phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 124476-96-6 phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 124477-03-8 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl phenyl sulphone 
• 124477-05-0 2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl phenyl sulphone 
• 124477-12-9 2,6-anhydro-5-deoxy-3,4-O-isopropylidene-D-arabino-hex-5-enitol 
• 161602-53-5 phenyl 2,6-di-O-benzoyl-3,4-O-[1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside 
• 161602-55-7 phenyl 2,6-di-O-benzoyl-3,4-O-[1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside 
• 161602-69-3 5-<(benzyloxycarbonyl)amino>pentyl 6-O-benzoyl-3,4-O-<1-(S)-(methoxycarbonyl)ethylidene>-2-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 161602-66-0 5-<(benzyloxycarbonyl)amino>pentyl 6-O-benzoyl-2-O-(2-chloroacetoxymethyl)benzoyl-3,4-O-<1-(R)-(methoxycarbonyl)ethylidene>-β-D-galactopyranoside 
• 161602-65-9 phenyl 6-O-benzoyl-2-O-(2-chloroacetoxymethyl)benzoyl-3,4-O-<1-(R)-(methoxycarbonyl)ethylidene>-1-thio-β-D-galactopyranoside 

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.

From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides

The treatment of various glycosyl acceptors, each containing a reactive thiol group, with the appropriate glycosyl donor and a glycoside hydrolase or glycosynthase, failed to yield any thioglycosides - only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.

PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULPHONES

Phenyl thioglycopyranosides with various protecting groups (acetal, ether, ester) underwent reductive lithiation at C-1, followed by rapid elimination of the 2-substituent, when treated with lithium naphthalenide in tetrahydrofuran at low temperature.Thus