35695-00-2

Upstream product

• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 106-45-6 para-thiocresol 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 84635-42-7 (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 

Downstream Products

• 1262201-86-4 p-tolyl 2-acetamido-6-O-acetyl-2-deoxythio-1-β-D-glucopyranoside 
• 1262201-88-6 p-tolyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-thio-1-β-D-glucopyranoside 
• 1262201-87-5 p-tolyl 2-acetamido-3,6-di-O-acetyl-2-deoxythio-1-β-D-glucopyranoside 

Relevant academic research and scientific papers

A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-d-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride and aryl thiols or disulfides

An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-β-d-glucopyranosides has been devised from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride and arylthiols or aryl disulfides using phase transfer catalysis condit

Reinvestigation of N, N-Diacetylimido-Protected 2-Aminothioglycosides in O-Glycosylation: Intermolecular Hydrogen Bonds Contributing to 1,2-Orthoamide Formation

N,N-Diacetylimido protection of 2-aminoglycosides is an elegant strategy but has had limited applications due to unexpected side reactions in glycosylation. We found that high acid concentrations could diminish the side reactions. We observed intermolecular hydrogen bonding among alcohols and acids could disrupt. Assuming that intermolecular hydrogen bonding accelerates the formation of 1,2-orthoamides and disrupting intermolecular hydrogen bonds could turn to the desired glycosylation, we successfully employed sulfenyl triflate pre-activation in the glycosylation of a broad scope of alcohol acceptors, as well as in a one-pot synthesis of a protected human milk oligosaccharide, lacto-N-neotetraose.

Chemoselective deacylation of functionalized esters catalyzed by dioxomolybdenum dichloride

Among five different oxidometallic species and two Lewis acids investigated, MoO2Cl2 shows the best catalytic and chemoselective activity for the deacylation of esters in methanol at ambient or elevated temperature. Both high efficiency and chemoselectivity were achieved for substrates bearing different ether or ester groups. Acylated mono and disaccharides can also be selectively deacetylated in good yields, leading to useful carbohydrate templates for further synthetic manipulations.

Synthesis and biological activity of aryl S-β-glycosides of 1-thio-N-acetylmuramyl-L-alanyl-D-isoglutamine

Phenyl, p-tolyl, and p-tert-butylphenyl β-1-thio-N- acetylglucosaminides were synthesized by the treatment of thiophenols with peracetate of α-D-glucosaminyl chloride in the presence of triethylamine or under the conditions of phase-transfer catalysis with quaternary ammonium salts. The compounds synthesized were used for obtaining of glycosides of 4,6-O-isopropylidene-N-acetylmuramic acid, which were coupled with L-Ala-D-Glu(NH2)-OBzl and then deprotected to obtain the target aryl β-thioglycosides of N-acetylmuramyl-L-analyl-D-isoglutamine (MDP). The aryl β-thioglycosides of MDP were found to stimulate an antibacterial resistance toward Staphylococcus aureus in mice. The reliable induction of the spontaneous activity of natural killers in the population of blood mononuclear cells was observed only for phenyl β-thio-MDP at a dose of 200 μg/ml.