97974-19-1

Upstream product

• 71676-30-7 phenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 152983-23-8 phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside 
• 108-98-5 thiophenol 
• 71676-30-7 (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 97974-28-2 C₄₉H₆₀O₂₄S 
• 947257-16-1 phenyl 2,3-di-O-acetyl-6-O-benzyl-4-O-(6-deoxy-2,3,4-tri-O-tert-butyldimethylsilyl-α-L-mannopyranosyl)-1-thio-β-D-glucopyranoside 
• 97974-37-3 C₆₀H₇₅FO₃₁ 
• 97974-29-3 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 1421280-32-1 thiophenyl 2,3-di-Ο-benzyl-4,6-Ο-benzylidene-β-D-mannopyranosyl-(1,4)-2,3-di-Ο-acetyl-6-Ο-benzyl-β-D-glucopyranoside 
• 162284-49-3 methyl 2,3-di-O-acetyl-6-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of new sulfated disaccharides for the modulation of TLR4-dependent inflammation

Natural sulfated glycans are key players in inflammation through TLR4 activation; therefore synthetic exogenous sulfated saccharides can be used to downregulate inflammation processes. We have designed and synthesized new sulfated compounds based on small and biocompatible carbohydrates that are able to cross the BBB. A suitable protected donor and acceptor, obtained from a unique precursor, have been stereoselectively glycosylated to give an orthogonally protected cellobiose disaccharide. Selective deprotection and sulfation allowed the syntheses of four differentially sulfated disaccharides, which have been characterized by NMR, HRMS and MS/MS. Together with their partially protected precursors, the new compounds were tested on HEK-TLR4 cells. Our results show the potential of small oligosaccharides to modulate TLR4 activity, confirming the need for sulfation and the key role of the 6-sulfate groups to trigger TLR4 signalization.

HClO4-silica-catalysed regioselective opening of benzylidene acetals and its application towards regioselective HO-4 glycosylation of benzylidene acetals in one-pot

Here we report a high-yielding method for the regioselective reductive ring opening of 4,6-O-benzylidene acetals of hexapyranosides using inexpensive and robust HClO4-SiO2 as the acidic catalyst and triethylsilane as the hydride dono

2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks

Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.

Copper(II) triflate: A versatile catalyst for the one-pot preparation of orthogonally protected glycosides

The development of general and expedient methodologies for the preparation of orthogonally protected glycoside building blocks is essential for the efficient synthesis of complex oligosaccharides. Herein, we describe a new approach that uses copper(II) triflate as a versatile catalyst for the one-pot preparation of orthogonal protected thio- and O-glycosides from the corresponding unprotected counterparts. The conditions are mild, easy to handle and applicable to two and three one-pot tandem transformations, which include arylidene acetalation, esterification, regioselective reductive acetal ring opening, glycosylation and silylation processes. Copyright