29073-91-4

Upstream product

• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 76985-96-1 3,4,6-tri-O-acetyl-1,2-O-(1-(exo-p-tolylthio)ethylidene)-beta-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 60426-93-9 3,4,6-tri-O-acetyl-1,2-O-(1-(exo-p-tolylthio)ethylidene)-alpha-D-glucopyranose 
• 60410-57-3 3,4,6-tri-O-acetyl-1,2-O-(1-(endo-p-tolylthio)ethylidene)-alpha-D-glucopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 530-26-7 D-Mannose 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 13242-53-0 acetobromomannose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 

Downstream Products

• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 163523-17-9 6-O-tert-Butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose 
• 324041-25-0 3,4,6-tri-O-benzoyl-1,2-O-[(RS)-1-methoxyethane-1,1-diyl]-β-D-mannopyranose 
• 383367-67-7 (3aS,5R,6R,7S,7aS)-7-Benzyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol 
• 68681-00-5 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 
• 484647-42-9 2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-D-mannopyranozyl trichloroacetimidate 
• 484647-54-3 benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside 
• 484647-69-0 benzyl 2-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-D-glycero-α-D-gluco-heptopyranoside 
• 146579-47-7 Octyl-O-<2,4,6-tri-O-acetyl-3-O-(4-pentenyl)-α-D-mannopyranosyl>-(1->6)-2,4-di-O-benzyl-β-D-mannopyranosid 
• 1363902-76-4 C₄₂H₄₈Cl₃NO₉Si 
• 1363902-60-6 6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(p-methoxybenzyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside 
• 1407151-89-6 p-tolyl 2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzylthio-α-D-mannopyranoside 
• 1407151-91-0 p-tolyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4,6-tri-O-benzylthio-α-D-mannopyranoside 
• 1407151-93-2 p-tolyl 3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-6-O-benzoyl-2,4-di-O-benzylthio-α-D-mannopyranoside 

Relevant academic research and scientific papers

A Concise Synthesis of Oligosaccharides Derived From Lipoarabinomannan (LAM) with Glycosyl Donors Having a Nonparticipating Group at C2

Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death over the world, and lipoarabinomannan (LAM) has been confirmed to play significant roles in this process. In this study, a convenient synthetic approach ha

β-Mannosylation through O-Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans

Several structurally diverse d-mannose-derived lactols, including various deoxy-d-mannoses and conformationally restricted bicyclic d-mannoses, have been synthesized and investigated in mechanistic studies of β-mannosylation through Cs2CO3-mediated anomeric O-alkylation. It was found that deoxy mannoses or conformationally restricted bicyclic d-mannoses are not as reactive as their corresponding parent mannose. This type of β-mannosylation proceeds efficiently when the C2-OH is left free, and protection of that leads to inferior results. NMR studies of d-mannose-derived anomeric cesium alkoxides indicated the predominance of the equatorial β-anomer after deprotonation. Reaction progress kinetic analysis suggested that monomeric cesium alkoxides be the key reactive species for alkylation with electrophiles. DFT calculations supported that oxygen atoms at C2, C3, and C6 of mannose promote the deprotonation of the anomeric hydroxyl group by Cs2CO3 and chelating interactions between Cs and these oxygen atoms favor the formation of equatorial anomeric alkoxides, leading to the highly β-selective anomeric O-alkylation. Based on experimental data and computational results, a revised mechanism for this β-mannosylation is proposed. The utilization of this β-mannosylation was demonstrated by an efficient synthesis of the hexasaccharide core of complex fucosylated N-linked glycans.

Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

RETRACTED ARTICLE: Chemical synthesis and antigenic activity of a phosphatidylinositol mannoside epitope from: Mycobacterium tuberculosis

Phosphatidylinositol mannosides (PIMs) have been investigated as lipidic antigens for a new subunit tuberculosis vaccine. A non-natural diacylated phosphatidylinositol mannoside (Ac2PIM2) was designed and synthesized by mimicking the natural PIM6 processi

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

Leishmaniasis, a neglected tropical disease, currently infects approximately 12 million people worldwide with 1 to 2 million new cases each year in predominately underdeveloped countries. The treatment of the disease is severely underdeveloped due to the

Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity

The total synthesis of the 20 homogeneous members of mannosylerythritol lipids (MELs) with different alkyl chain lengths was effectively and systematically accomplished from a strategically designed common key intermediate that was stereoselectively constructed by the borinic acid catalyzed β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated. Our results demonstrated that not only the length of the alkyl chains but also the pattern of Ac groups on the mannose moiety were important factors for antibacterial activity.

Targeted delivery of fluorescent high-mannose-type oligosaccharide cathepsin inhibitor conjugates

Abstract Three fluorescent cathepsin inhibitor glycoconjugates have been designed, synthesized, and evaluated in terms of their cell internalization and cathepsin inhibitory properties. The conjugates are composed of a peptide epoxysuccinate, capable of c

Concise synthesis and antidiabetic effect of three natural triterpenoid saponins isolated from Fadogia ancylantha (Makoni tea)

The first concise synthesis of the bidesmosidic oleanolic acid saponins 1-3 isolated from Fadogia ancylantha (Makoni tea) have been accomplished through a 'one-pot sequential glycosylation' strategy with two glycosyl 1-(trichloroacetimidate)s as glycosyl donors. The synthesized natural products 1-3 were then evaluated for their inhibitory activities against α-glucosidase, α-amylase, and lipase. Among the assayed compounds 1-3, compound 1 showed strong α-glucosidase and α-amylase inhibition, with IC50 values of 160 and 180 μM, respectively. Moreover, compounds 2 and 3 showed strong inhibition against α-glucosidase and lipase, with the respective IC50 values of 170 and 190 μM, and 190 and 200 μM.

Exploring glycosylation reactions under continuous-flow conditions

The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.

Total synthesis of a glycosylphosphatidylinositol anchor of the human lymphocyte CD52 antigen

The first total synthesis of a glycosylphosphatidylinositol (GPI) anchor bearing a polyunsaturated arachidonoyl fatty acid is reported. This lipid is found in mammalian GPIs that do not undergo lipid remodeling, a process that has important implications in the localization and function of GPI-anchored proteins. Incorporation of the oxidation- and reduction-sensitive arachidonoyl lipid in the target GPI was accomplished by using the para-methoxybenzyl (PMB) group for permanent hydroxyl group protection, which featured a selective, rapid, and efficient global deprotection protocol. The flexibility of this synthetic strategy was further highlighted by the inclusion of two additional GPI core structural modifications present in the GPI anchor of the human lymphocyte CD52 antigen. Lipid diversity in GPI synthesis: The convergent synthesis of an arachidonoyl-containing glycosylphosphatidylinositol (GPI) anchor of the human lymphocyte CD52 antigen is reported. Incorporation of the oxidation- and reduction-sensitive polyunsaturated arachidonoyl lipid, as well as two additional GPI core modifications (see structure), was enabled by using a para-methoxybenzyl (PMB)-based global protection strategy. Copyright