94943-10-9

Usage

Type of compound

Mannopyranose
Mannopyranose is a six-carbon sugar derived from plant polysaccharides. It is a type of monosaccharide, which is the simplest form of carbohydrates.

Synthesis method

Acetylation and benzylation
The compound is synthesized by modifying the D-mannopyranose molecule. The hydroxyl group at the 1 position is acetylated (addition of an acetyl group), and the hydroxyl groups at the 2, 3, 4, and 6 positions are benzylated (addition of benzyl groups).

Use in organic synthesis

Building block for complex compounds
1-O-ACETYL-2,3,4,6-TETRA-O-BENZYL-D-MANNOPYRANOSE is commonly used as a building block in organic synthesis to create more complex chemical compounds.

Protecting groups

Benzyl groups
The benzyl groups in the molecule act as protecting groups for the hydroxyl groups. This allows for selective reactions during the synthesis process, preventing unwanted side reactions and ensuring the desired product is formed.

Upstream product

• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 108-24-7 acetic anhydride 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 75-36-5 acetyl chloride 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 1438395-04-0 C₈H₁₄O₇ 
• 100-39-0 benzyl bromide 
• 530-26-7 D-Mannose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 90358-01-3 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 
• 64-19-7 acetic acid 
• 53081-25-7 2,3,4,6-tetra-O-benzyl-D-galactopyranose 

Downstream Products

• 785806-29-3 thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside 
• 126252-57-1 β-D-galactopyranosyl 1-acetate 
• 149270-66-6 2,3,4,6-Tetra-O-benzyl-β-D-galactopyranosylphosphonsaeure-dimethylester 
• 443915-85-3 trimethyl-[2-[(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 1038507-81-1 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranose 
• 53081-25-7 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 287962-77-0 (2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyl-tetrahydropyran 
• 156407-74-8 benzyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 4132-31-4 benzyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

A general approach to C-Acyl glycosides via palladium/copper Co-catalyzed coupling reaction of glycosyl carbothioates and arylboronic acids

A general and efficient approach to the synthesis of various C-acyl glycosides has been developed via Pd2(dba)3/CuTC co-catalyzed cross-coupling reaction of glycosyl carbothioates with arylboronic acids. The reaction showed a broad s

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

IMPROVED PROCESS FOR PREPARATION OF 2,3,4,6-TETRA-O-BENZYL-D-GALACTOSE

Provided herein is an improved process for the preparation of benzylated derivative of D-galactose, particularly 2,3,4,6-tetra-O-benzyl-D-galactose that gives higher yield and better purity being cost effective with reduced impurities.

Addition of Organozinc Reagents to Glycopyranosyl Cyanides: Access to Keto Ester-C-glycosides or Unsaturated Acyl-C-glycosides

Addition of Reformatsky-type or allylic zinc reagents to 2,3,4,6-tetra-O-benzylglycopyranosyl cyanides led to keto ester-C-glycosides or unsaturated acyl-C-glycosides in moderate to excellent yields in the galactose, glucose, and mannose series.

C-GLYCOSIDE COMPOUNDS USEFUL FOR TREATING DISEASE

The present invention relates to mannoside derivative compounds useful as inhibitors of FimH and methods for the treatment or prevention of urinary tract infection.

MANNOSE-DERIVED ANTAGONISTS OF FIMH USEFUL FOR TREATING DISEASE

The present invention relates to mannoside derivative compounds useful as inhibitors of FimH and methods for the treatment or prevention of urinary tract infection.

Novel glycolipid TLR2 ligands of the type Pam2Cys-α-Gal: Synthesis and biological properties

A more complete understanding of the mechanism of action of TLR agonists has fueled the investigation of new synthetic immunoadjuvants. In this context, we designed and synthesized glycolipids of the type Pam2Cys-α- Galactose as novel immunoadj

Monosaccharidic mimetics of the sialyl LewisX tetrasaccharide based on 2,7-dihydroxynaphthalene

A potential monosaccharidic mimetic of the sialyl LewisX tetrasaccharide (sLeX) was identified based on an in silico docking study using the crystal structure of an E-selectin-sLeX complex. The chemical synthesis of the mimetic in an ortho-selective C-glycosylation is described. This compound and two close analogues were evaluated in a cell-based selectin binding assay where none of the tested mimetics showed an IC 50 below 1mM. This result can be explained by an unexpected 1C4 conformation of the mannosyl residue which precludes the required binding of the Ca2+-ion in E-selectin.

Synthesis of 1,2,3-triazole linked galactopyranosides and evaluation of cholera toxin inhibition

We report the synthesis of a series of bivalent 1,2,3-triazole linked galactopyranosides as potential inhibitors of cholera toxin (CT). The inhibitory activity of the bivalent series was examined (ELISA) and the series showed low inhibitory activity (millimolar IC50s). Conversely, the monomeric galactotriazole analogues were strong inhibitors of cholera toxin (IC 50 = 71-75 μM). The Royal Society of Chemistry 2011.

Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry

KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release a broad range of bioactive cytokines. In an effort to understand the structure-activity relationships, we have carried out synth