56083-16-0

Usage

Molecular Structure

A galactose molecule with an allyl group at the 1-position and benzyl groups at the 2, 3, and 4 positions.

Type of Compound

A chemical compound.

Usage

Commonly used as a building block in organic synthesis.

Specific Application

Preparation of carbohydrate derivatives.

Role in Glycosylation

Acts as a glycosyl donor in glycosylation reactions.

Capability

Can be employed in the creation of complex carbohydrate structures.

Potential Applications

May have applications in the field of medicinal chemistry.

Influence on Biological Molecules

Ability to modify biological molecules and influence their function.

Upstream product

• 100759-11-3 allyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-α-D-galactopyranoside 
• 48149-72-0 (2S,3R,4S,5R,6R)-2-Allyloxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 258854-17-0 1-O-Allyl 6-O-trityl-α-D-galactopyranoside 
• 617-86-7 triethylsilane 
• 100-39-0 benzyl bromide 
• 100759-10-2 allyl 4,6-di-O-benzylidene-α-D-galactopyranoside 
• 2595-07-5 allyl D-galactopyranoside 
• 10257-28-0 D-Galactose 

Downstream Products

• 2771-55-3 2,3,4-tri-O-benzyl-D-galactopyranoside 
• 289893-54-5 2,3,4-tri-O-benzyl-1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-α-D-galactose 
• 912650-64-7 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-galacto-hept-2-ulosyl-(2->6)-2,3,4-tri-O-benzyl-D-galactono-1,5-lactone 
• 912651-01-5 2,3,4-tri-O-benzyl-D-galactono-1,5-lactone 

Relevant academic research and scientific papers

CARBOHYDRATE-GLYCOLIPID CONJUGATE VACCINES

The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

POLYSACCHARIDE ANTIGEN-GLYCOLIPID CONJUGATE VACCINES

The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3

The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

PROTEIN AND PEPTIDE-FREE SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 3

The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.