4356-82-5

Usage

Uses

Used in Carbohydrate Chemistry:
Methyl 2,3,4-tris-O-(phenylmethyl)-beta-D-glucopyranosiduronic acid is used as a building block in carbohydrate chemistry for the synthesis of various carbohydrate-based molecules. Its unique structure allows for the creation of complex and diverse molecules with potential applications in different industries.
Used in Pharmaceutical Applications:
Due to its potential biological activities, Methyl 2,3,4-tris-O-(phenylmethyl)-beta-D-glucopyranosiduronic acid may be studied for its possible use in pharmaceutical applications. Its unique structure could provide new avenues for drug development, particularly in the synthesis of novel therapeutic agents.
Used in Medical Applications:
Methyl 2,3,4-tris-O-(phenylmethyl)-beta-D-glucopyranosiduronic acid may also be explored for its potential use in medical applications. Its unique properties could contribute to the development of new diagnostic tools, imaging agents, or therapeutic interventions in the medical field.

InChI:InChI=1/C28H30O7/c1-31-28-26(34-19-22-15-9-4-10-16-22)24(33-18-21-13-7-3-8-14-21)23(25(35-28)27(29)30)32-17-20-11-5-2-6-12-20/h2-16,23-26,28H,17-19H2,1H3,(H,29,30)/t23-,24-,25-,26+,28+/m0/s1

Upstream product

• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 40653-30-3 methyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-galactopyranoside 
• 18311-26-7 methyl 6-O-triphenylmethyl-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 

Downstream Products

• 4356-83-6 benzyl 1-O-methyl-2,3,4-tri-O-benzyl-β-D-glucopyranuronate 
• 10357-03-6 Methyl-(methyl-D-galactopyranosid) uronate, β anomer 
• 62435-44-3 methyl (methyl 2,3,4-tri-O-benzyl-β-D-galactopyranosid)uronate 
• 117192-23-1 (E)-(R)-3-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol 
• 117174-45-5 (E)-3-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenone 
• 117192-22-0 2-(Triphenyl-λ⁵-phosphanylidene)-1-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethanone 

Relevant academic research and scientific papers

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

From d-to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation

Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.

A NEW CONVENIENT APPROACH TO HIGHER SUGAR ALLYLIC ALCOHOLS

Allylic alcohol 4, a chiral synthon for the preparation of des-aza tunicamine (2), was obtained by two independent routes starting from either D-galactose or D-ribose derivatives.The selection of the starting material depends, therefore, only on its availability.The interchangeability of the synthetic routes is especially important when rare sugars have to be used in the synthesis.