108869-64-3

Upstream product

• 129214-38-6 2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside 
• 545-06-2 trichloroacetonitrile 
• 79218-68-1 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 29073-91-4 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 100-39-0 benzyl bromide 
• 83-87-4 D-Mannose pentaacetate 
• 13242-53-0 acetobromomannose 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 88988-46-9 2-O-acetyl-3,4,6-tetra-O-benzyl-α-D-glucopyranose 
• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 
• 64-19-7 acetic acid 
• 65827-55-6 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 136945-11-4 8-Methoxycarbonyloctyl-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid 
• 146579-74-0 Octyl-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-benzyl-4,6-O-isopropyliden-β-mannopyranosid 
• 225924-67-4 allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside 
• 172539-80-9 Octyl-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-3-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosid 
• 189745-77-5 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 206866-63-9 C₇₀H₈₅N₃O₁₆Si 
• 206866-65-1 C₉₉H₁₁₇N₃O₂₂Si 
• 68601-72-9 methyl 2,4-di-O-benzyl-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→3))-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→6))-α-D-mannopyranoside 
• 220734-61-2 4-methoxyphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives

Thioglycosides are more resistant to enzymatic hydrolysis than their O-linked counterparts, thereby becoming attractive targets for carbohydrate-based therapeutic development. We report the first development of methods for the site-selective incorporation

Lithium triflate as a new promoter of glycosylation under neutral conditions

The glycosyl donors 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate and 3,4,6-tri-O-benzyl-α-D-fucopyranosyl trichloroacetimidate were activated under neutral conditions with a catalytic amount (0.05 equiv) of lithium triflate and reacted w

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

Concise Total Synthesis of Peyssonnoside A

Peyssonnoside A is a marine-derived sulfated diterpenoid glucoside with a unique 5/6/3/6 tetracyclic skeleton with a highly substituted cyclopropane ring deeply embedded into the structure. Herein, we report the first total synthesis of this natural product in a concise, efficient, scalable, and highly diastereoselective fashion. The aglucone peyssonnosol was synthesized in 21% overall yield after 15 steps, featuring a Simmons-Smith cyclopropanation and Mukaiyama hydration, fully controlled by the spatial structure of the substrates.

Total Synthesis of Myrmekioside A, a Mono-O-alkyl-diglycosylglycerol from Marine Sponge Myrmekioderma sp.

Myrmekioside A, which was isolated from the marine sponge Myrmekioderma sp. as a member of the family of natural mono-O-alkyl-diglycosylglycerols, and which has a strong reversion effect on the tumor cell morphology of ras-transformed cells at 5 μg/mL, wa

Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates

Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har

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.

Intramolecular aglycon delivery for (1 → 2)-β-mannosylation: Towards the synthesis of phospholipomannan of Candida albicans

A high yielding method for 1,2-cis-β-D-mannosylation by intra-molecular aglycon delivery (IAD) through p-methoxy benzyl ether/acetal exchange and phenylsulfoxide donor is reported, along with its application in iterative assembly of antigenic (1 → 2)-β-pe

'Naked' and hydrated conformers of the conserved core pentasaccharide of N-linked glycoproteins and its building blocks

N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man3GlcNAc2- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-β-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-α-1,3- and Man-α-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a β-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.

Synthesis of tri- and tetra-mannosides based on sequential one-pot three-component glycosylation reactions

Expeditious syntheses of tri- and tetra-mannosides were carried out based on sequential one-pot glycosylation strategy. In both of these syntheses TMSOTf activated trichloroacetimidate, the first glycosyl donor, and inexpensive readily accessible trichlor