57817-52-4

Upstream product

• 112716-28-6 methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-galactopyranoside 
• 106248-66-2 1,2,3,4-tetra-O-acetyl-6-O-(p-tolylsulfonyl)-β-D-galactopyranose  
• 121424-21-3 O¹,O²,O³,O⁴-tetraacetyl-O⁶-(toluene-4-sulfonyl)-α-D-galactopyranose 
• 13046-90-7 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-galactosyl bromide 
• 67-56-1 methanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1824-94-8 methyl beta-D-galactopyranoside 

Downstream Products

• 112716-28-6 methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-galactopyranoside 
• 75869-74-8 3,6-anhydro-D-lyxo-hexosulose 1,2-bis(phenylhydrazone) 
• 14122-18-0 3,6-anhydro-D-galactose 
• 357953-00-5 methyl 2,3,4-tri-O-acetyl-6-thio-6-[2'-(methyl 2-phenylacetate)]-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of positional thiol analogs of β-D-galactopyranose

Approaches toward the synthesis of thio-β-D-galactose derivatives are described. These compounds were prepared from the parent carbohydrates: D-galactose, methyl β-D-galactoside and methyl β-D-glucoside, respectively. It was found that not only the strategies of protecting group introduction and selective deprotection, but also the choices of solvent and nucleophilic reagent concentration were crucial to allow the efficient introduction of sulfur at different positions of the galactose ring. The effects from the solvent, the nucleophilic reagent concentration, and the protecting group patterns have been investigated. The results clearly show that ester protecting groups play highly important roles for the synthesis of thio-containing carbohydrates, requiring nonpolar solvents to suppress the neighboring group participation. For the Lattrell-Dax (nitrite-mediated) inversion reaction, employed in the synthetic route to the 2-thio-β-D- galactoside, intramolecular nucleophilic attack, as well as stronger stereospecific ester activation, are necessary to overcome hindrance from 4,6-O-benzylidene protection. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

TBAF Effects 3,6-Anhydro Formation from 6-O-Tosyl Pyranosides

3,6-Anhydro sugars are common structures in algal polysaccharides and occur in the furanodictine and sauropunol natural products. We have found that treatment of 6-O-tosylpyranosides with tetrabutylammonium fluoride provides a mild, high-yielding synthesis of 3,6-anhydro sugars. Using O-glycoside substrates, 3,6-anhydropyranosides are isolated and the use of N,O-dimethyl hydroxylamine glycosides yields 3,6-anhydrofuranosides. Applying this approach, concise synthetic routes to several 3,6-anhydro sugar natural products are reported, including furanodictine A and sauropunols A-D.

'Click chemistry' synthesis of a library of 1,2,3-triazole-substituted galactose derivatives and their evaluation against Trypanosoma cruzi and its cell surface trans-sialidase

Trypanosoma cruzi trans-sialidase (TcTS) plays a key role in the recognition and invasion of host cells and in enabling the parasite to escape the human immune response. To explore this potential drug target, we have synthesized a small library of substra

Synthesis of novel sialylmimetics as biological probes

Glycomimetics are increasingly being recognised as powerful tools in the search for novel compounds that possess useful biological properties. This paper describes our preliminary efforts towards the development of novel mimetics of sialic acid thioglycosides. These sialylmimetics are readily prepared and have been shown, in some instances, to have biological properties similar to sialic acid thioglycosides. Elsevier Science Ltd. All rights reserved.

Synthesis and biological evaluation of sialylmimetics as rotavirus inhibitors

Rotaviruses cause severe gastroenteritis in infants and are estimated to be responsible for over 600 000 deaths annually, primarily in developing countries. The development of potential inhibitors of this virus is therefore of great interest, particularly since the safety and efficacy of rotaviral vaccines has recently been questioned. This study describes the synthesis of a variety of compounds that can be considered as mimetics of N-acetylneuraminic acid thioglycosides and the subsequent in vitro biological evaluation of these sialylmimetics as inhibitors of rotaviral infection. Our results show that readily accessible carbohydrate-based compounds have the potential to act as inhibitors of rotaviral replication in vitro, presumably through inhibition of the rotaviral adhesion process.