16697-49-7

Usage

Uses

Used in Organic Synthesis:
3,4,6-Tri-O-benzyl-beta-D-mannopyranose-1,2-(methyl orthoacetate) is used as a synthetic intermediate for organic synthesis, particularly in the preparation of complex carbohydrates and glycoconjugates. Its unique structure allows for the selective removal of protecting groups, enabling the synthesis of a wide range of carbohydrate derivatives with specific properties and functions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4,6-Tri-O-benzyl-beta-D-mannopyranose-1,2-(methyl orthoacetate) is used as a key building block for the development of glyco-based drugs. Its ability to form glycosidic linkages with various aglycones makes it a valuable tool for the synthesis of bioactive compounds with potential therapeutic applications.
Used in Chemical Research:
3,4,6-Tri-O-benzyl-beta-D-mannopyranose-1,2-(methyl orthoacetate) is also used in chemical research as a model compound for studying the reactivity and selectivity of glycosylation reactions. Its well-defined structure allows researchers to investigate the influence of protecting groups and reaction conditions on the outcome of glycosylation processes, contributing to the advancement of carbohydrate chemistry.

InChI:InChI=1/C30H34O7/c1-30(31-2)36-28-27(34-20-24-16-10-5-11-17-24)26(33-19-23-14-8-4-9-15-23)25(35-29(28)37-30)21-32-18-22-12-6-3-7-13-22/h3-17,25-29H,18-21H2,1-2H3/t25?,26-,27+,28-,29+,30?/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 29073-91-4 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 100-44-7 benzyl chloride 
• 83-87-4 D-Mannose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 67-56-1 methanol 
• 13242-53-0 acetobromomannose 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 29073-91-4 (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 117703-05-6 6-(N-benzyloxycarbonylamino)-hexyl-2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 20672-69-9 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 129214-38-6 2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside 
• 93381-69-2 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl bromide 
• 68567-54-4 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 65827-57-8 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose 
• 138181-67-6 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 130525-72-3 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 911291-36-6 3,4,6-tri-O-benzyl-β-D-mannopyranose 
• 65827-56-7 3,4,6-Tri-O-benzyl-D-mannose 
• 164923-33-5 pyridin-2-yl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 197158-97-7 benzothiazol-2-yl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 674303-02-7 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl azide 
• 681831-82-3 4-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

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

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

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

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

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

ANTIBODY CONJUGATES AND METHODS OF MAKING THE ANTIBODY CONJUGATES

Described herein are antibody conjugates and methods of making antibody conjugates.

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

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.

Synthesis of a tristearoyl lipomannan via preactivation-based iterative one-pot glycosylation

A convergent and efficient strategy was developed for the synthesis of lipomannan (LM), useful for vaccine development. Thioglycosides were employed as glycosyl donors to construct two key pseudotrisaccharide and tetramannose intermediates through preacti