220645-20-5

Upstream product

• 122210-05-3 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose 
• 106-45-6 para-thiocresol 
• 122210-01-9 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 323195-39-7 p-methylphenyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 
• 90-76-6 2-deoxy-2-amino glucose 
• 136945-13-6 [(2R,3S,4R,5R)-3,4-diacetoxy-6-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)tetrahydropyran-2-yl]methyl acetate 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 

Downstream Products

• 323195-45-5 p-methylphenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 
• 852570-15-1 p-methylphenyl 4,6-O-p-methoxybenzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 
• 852570-18-4 p-methylphenyl 3-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 
• 852570-16-2 p-methylphenyl 3-O-benzoyl-4,6-O-p-methoxybenzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 
• 145383-38-6 methyl O-<3,4,6-tri-O-acetyl-2-deoxy-(2,2,2-trichloroethoxycarbonyl)amino)-β-D-glucopyranosyl>-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 133940-44-0 benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 1616703-76-4 28-O-benzyl-3-O-[3′,4′,6′-tri-O-acetyl-2′-deoxy-2′-(2″,2″,2″-trichloroethyloxycarbonylamino)-β-D-glucopyranosyl]oleanolic ester 

Relevant academic research and scientific papers

Design, synthesis and cytotoxic activity of N-Modified oleanolic saponins bearing A glucosamine

A series of N-acyl, N-alkoxycarbonyl, and N-alkylcarbamoyl derivatives of 2′-deoxy-glucosyl bearing oleanolic saponins were synthesized and evaluated against HL-60, PC-3, and HT29 tumor cancer cells. The SAR studies revealed that the activity increased in order of conjugation of 2′ -amino group with carbamate > amide > urea derivatives. Lengthening the alkyl chain increased the cytotoxicity, the peak activity was found to around heptyl to nonyl substitutions. 2′-N-heptoxycarbonyl derivative 56 was found to be the most cytotoxic (IC50 = 0.76 μM) against HL-60 cells. Due to the interesting SARs of alkyl substitutions, we hypothesized that their location in the cell was different, and pursued a location study using 2′-(4″-pentynoylamino) 2′-deoxy-glucosyl OA, which suggested that these compounds distributed mainly in the cytosol.

A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa

Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained wi

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

Low-concentration 12-trans β-selective glycosylation strategy and its applications in oligosaccharide synthesis

This study develops an operationally easy, efficient, and general 1,2-trans β-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans β-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans β-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant β-(1-6)-glucan trisaccharide, β-linked Gb3 and isoGb3 derivatives.

Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides

Inexpensive and readily available sulfonic acids, p-toluenesulfonic acid, and sulfuric acid are versatile and efficient catalysts for the peracetylation of a broad spectrum of carbohydrate substrates in good yield and in a practical time frame. Three appealing features in sulfonic acid-catalyzed acetylation of free sugars were explored including (1) suppression of furanosyl acetate formation for d-galactose and l-fucose; (2) high yielding chemoselective acetylation of sialic acid under appropriate conditions; and (3) peracetylation of amino sugars with different amino protecting functions. Simple one-pot two step acetylation-thioglycosidation methods for the expeditious synthesis of p-tolyl per-O-acetyl thioglycosides were also delineated.

Studies directed to the synthesis of oligochitosans - Preparation of building blocks and their evaluation in glycosylation studies

Thioglucosaminides with four different N-protecting groups, Troc, Phth, Alloc and PNZ could selectively be benzoylated at the C3 and C6-hydroxy groups in good yields without the requirement for low-temperature techniques. These reactions could be performe

Large-scale synthesis of per-O-acetylated saccharides and their sequential transformation to glycosyl bromides and thioglycosides

This work describes a large-scale synthesis of per- O -acetylated mono- and disaccharides using a stoichiometric amount of acetic anhydride in the presence of LiClO 4 under solvent-free conditions. The peracetylated saccharides underwent subsequent anomeric bromination and thioglycosidation in one-pot to yield synthetically valuable building blocks. Copyright Taylor & Francis Group, LLC.

Characterization of a transglycosylase domain of Streptococcus pneumoniae PBP1b

Inhibitors of transglycosylases may serve as potent antibiotics that are less prone to resistance development in bacterial pathogens. To facilitate the search of such compounds, a transglycosylase (TGase) domain of the membrane integral multidomain Strept

Synthesis of peptidoglycan units with UDP at the anomeric position

A series of UDP-disaccharide peptide compounds were synthesized as synthetic substrate analogues or potential inhibitors of glycosyl transferase. Fluorescent compounds have been prepared with the aim of developing a screening method for selecting transglycosylase inhibitors.

Simple and efficient per-O-acetylation of carbohydrates by lithium perchlorate catalyst

Lithium perchlorate is demonstrated to be a highly efficient and convenient catalyst for the per-O-acetylation of various saccharides with excellent yields. Graphical Abstract