920267-56-7

Basic information

• Product Name: 4-methylphenyl 1-thio-β-D-galactofuranoside
• Synonyms: 4-methylphenyl 1-thio-β-D-galactofuranoside
• CAS NO: 920267-56-7
• Molecular Weight: 286.349
• Mol File: 920267-56-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-methylphenyl 1-thio-β-D-galactofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylphenyl 1-thio-β-D-galactofuranoside(920267-56-7)
• EPA Substance Registry System: 4-methylphenyl 1-thio-β-D-galactofuranoside(920267-56-7)

Safety Data

• Hazardous Substances Data: 920267-56-7(Hazardous Substances Data)

Upstream product

• 90244-45-4 methyl 2,3,5,6-tetra-O-acetyl-α/β-D-galactofuranoside 
• 106-45-6 para-thiocresol 
• 1033560-31-4 4-methylphenyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside 

Downstream Products

• 848900-41-4 p-tolyl 5,6-O-isopropylidene-1-thio-β-D-galactofuranoside 
• 920267-59-0 p-tolyl 2,3-anhydro-1-thio-β-D-gulofuranoside 
• 848900-39-0 p-tolyl 2,3-anhydro-5,6-O-isopropylidene-1-thio-β-D-gulofuranoside 
• 920267-51-2 p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside 
• 920267-52-3 p-tolyl 2,3-anhydro-5,6-di-O-benzoyl-1-thio-β-D-gulofuranoside 
• 920274-28-8 2,3-anhydro-5,6-di-O-benzoyl-β-D-gulofuranosyl-p-tolyl-(R/S)-sulfoxide 

Relevant articles and documents

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 galactofuranose-containing acceptor substrates for mycobacterial galactofuranosyltransferases

(Chemical Equation Presented) The major structural component of the cell wall in Mycobacterium tuberculosis, infection by which causes tuberculosis, is the mycolyl-arabinogalactan (mAG) complex. This large glycoconjugates has at its core a backbone of ～30 D-galactofuranose (Galf) residues that are linked to peptidoglycan by way of a linker disaccharide containing L-rhamnose and 2-acetamido-2-deoxy-D-glucose. Recent studies have supported a model of galactan biosynthesis in which the entire structure is assembled by the action of two bifunctional galactofuranosyltransferases. These biochemical investigations were made possible, in part, by access to a panel of oligosaccharide fragments of the mAG complex (1-12), the synthesis of which we describe here. An early key finding in this study was that the iodine-promoted cyclization of galactose diethyl dithioacetal (19) in the presence of an alcohol solvent led to the formation Galf glycosides contaminated with no pyranoside isomer, thus allowing the efficient preparation of furanoside derivatives of this monosaccharide. The synthesis of disaccharide targets 1, 2, 11 and 12 proceeded without difficulty through the use of thioglycoside donors and octyl glycoside acceptors, both carrying benzoyl protection. In the synthesis of the tri- and tetrasaccharides 3-6, we explored routes in which the molecule was assembled from the reducing to nonreducing end, and the reverse. The latter approach was found to be preferable for the preparation of 6, and in the case of 3 and 4, this strategy allowed the development of efficient one-pot methods for their synthesis. We have also carried out the first synthesis of three mAG fragments (8-10) consisting of the linker disaccharide further elaborated with one, two or three Galf residues. A key step in the synthesis of these target compounds was the coupling of a protected linker disaccharide derivative (58) with a mono-, di-, or trigalactofuranosyl thioglycoside (17, 54, or 53, respectively).