131897-00-2

Usage

Uses

Used in Organic Synthesis:
1,3,4-tri-O-benzyl-D-ribitol is used as a protecting group for hydroxyl functional groups, enabling the selective removal of these groups to reveal the original hydroxyl groups and facilitate further chemical reactions in the synthesis of complex organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1,3,4-tri-O-benzyl-D-ribitol is employed as a crucial intermediate in the synthesis of various pharmaceuticals. Its ability to protect hydroxyl groups allows for the controlled formation of complex molecular structures, which is vital for the development of new drugs and medicinal compounds.

Upstream product

• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 131896-99-6 methyl 2,3,5-tri-O-benzyl-α-L-ribofuranoside 
• 122565-72-4 2,3,5-tri-O-benzyl-D-lyxitol 
• 16838-89-4 2,3,5-tri-O-benzyl-α-L-ribofuranose 
• 41546-21-8 L-ribose 
• 52689-55-1 methyl α-L-ribofuranoside 
• 16838-89-4 2,3,5-tri-O-benzyl-D-lyxofuranoside 
• 872217-36-2 2,3,5-tri-O-benzyl-1-O-tert-butyldimethylsilyl-D-lyxitol 

Downstream Products

• 122501-70-6 1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol 
• 16838-89-4 2,3,5-tri-O-benzyl-α-L-ribofuranose 
• 131771-55-6 1,3,4-tri-O-benzyl-2-O-<2-O-(benzyloxymethyl)-5-O-(dimethoxytrityl)-β-D-ribofuranosyl>-5-O-(dimethoxytrityl)-D-ribitol 
• 131771-53-4 1,3,4-tri-O-benzyl-2-O-<2-O-(benzyloxymethyl)-5-O-4,4'-dimethoxytrityl-β-D-ribofuranosyl>-5-O-pivaloyl-D-ribitol 
• 131771-48-7 2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol 
• 131771-54-5 1,3,4-tri-O-benzyl-2-O-<2-O-(benzyloxymethyl)-5-O-(dimethoxytrityl)-β-D-ribofuranosyl>-D-ribitol 
• 131771-51-2 1,3,4-tri-O-benzyl-5-O-pivaloyl-2-O-<2-O-(benzyloxymethyl)-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-D-ribitol 
• 131771-50-1 1,3,4-tri-O-benzyl-5-O-pivaloyl-2-O-<3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-D-ribitol 
• 131771-52-3 1,3,4-tri-O-benzyl-2-O-<2-O-(benzyloxymethyl)-β-D-ribofuranosyl>-5-O-pivaloyl-D-ribitol 
• 131771-49-8 1,3,4-tri-O-benzyl-5-O-pivaloyl-2-O-(β-D-ribofuranosyl)-D-ribitol 
• 872217-37-3 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-lyxitol 

Relevant academic research and scientific papers

Azasugar inhibitors as pharmacological chaperones for Krabbe disease

Krabbe disease is a devastating neurodegenerative disorder characterized by rapid demyelination of nerve fibers. This disease is caused by defects in the lysosomal enzyme β-galactocerebrosidase (GALC), which hydrolyzes the terminal galactose from glycosphingolipids. These lipids are essential components of eukaryotic cell membranes: substrates of GALC include galactocerebroside, the primary lipid component of myelin, and psychosine, a cytotoxic metabolite. Mutations of GALC that cause misfolding of the protein may be responsive to pharmacological chaperone therapy (PCT), whereby small molecules are used to stabilize these mutant proteins, thus correcting trafficking defects and increasing residual catabolic activity in cells. Here we describe a new approach for the synthesis of galacto-configured azasugars and the characterization of their interaction with GALC using biophysical, biochemical and crystallographic methods. We identify that the global stabilization of GALC conferred by azasugar derivatives, measured by fluorescence-based thermal shift assays, is directly related to their binding affinity, measured by enzyme inhibition. X-ray crystal structures of these molecules bound in the GALC active site reveal which residues participate in stabilizing interactions, show how potency is achieved and illustrate the penalties of aza/iminosugar ring distortion. The structure-activity relationships described here identify the key physical properties required of pharmacological chaperones for Krabbe disease and highlight the potential of azasugars as stabilizing agents for future enzyme replacement therapies. This work lays the foundation for new drug-based treatments of Krabbe disease.

Synthesis of D-lyxitol and D-ribitol analogues of the naturally occurring glycosidase inhibitor salacinol

The synthesis of analogues of the naturally occurring glycosidase inhibitor, salacinol, in which the d-arabinitol ring has been replaced by d-lyxitol or d-ribitol, is described. Salacinol is one of the active principles in the aqueous extracts of Salacia reticulata, which are traditionally used in India and Sri Lanka for the treatment of Type II diabetes. The synthetic strategy relies on the nucleophilic attack of 1,4-anhydro-2,3,5-tri-O-p- methoxybenzyl-4-thio-d-lyxitol or 1,4-anhydro-2,3,5-tri-O-p-methoxybenzyl-4- thio-d-ribitol at the least hindered carbon of the benzylidene-protected l-cyclic sulfate derived from l-erythritol. Screening of these compounds against recombinant human maltase glucoamylase (MGA), a critical intestinal glucosidase involved in the processing of oligosaccharides of glucose into glucose itself, shows that they are not effective inhibitors of MGA and demonstrates the importance of the d-arabinitol configuration in the heterocyclic ring for effective inhibition.

Synthesis of a spacer-containing trimeric fragment of the capsular polysaccharide from Escherichia coli K100

Stereoselective β-glycosidation of 1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol, prepared from L-ribose, with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose gave, after protecting-group manipulations, the properly protected terminal and non-terminal units.Elongation (2*) of the terminal unit with the incoming non-terminal unit could be acomplished using the bifunctional phosphorylating reagent, bis(1-benzotriazolyl) 2-chlorophenyl phosphate.The trimeric unit thus obtained was condensed, using the same phosphorylating reagent, with the spacer N2-(benzyloxycarbonyl)-N1-(3-hydroxypropyl)glycinamide, to give, after complete deblocking, the spacer-containing trimeric unit of Escherichia coli K100.