81369-73-5

Upstream product

• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 18311-26-7 methyl 6-O-triphenylmethyl-β-D-galactopyranoside 
• 40653-30-3 methyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-galactopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 20231-36-1 methyl 6-O-trityl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 530-26-7 D-Mannose 
• 2595-06-4 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran 

Downstream Products

• 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 
• 862730-71-0 methyl 6-O-(4',6'-O-benzylidene-3'-O-yl-D-allal)-2,3,4-tri-O-benzyl-α-D-mannuronic ester 
• 862730-77-6 methyl 1,5-anhydro-6-O-(4',6'-O-benzylidene-3'-O-yl-D-allal)-7-deoxy-2,3,4-tri-O-benzyl-α-D-manno-hept-6-enopyranose 
• 81308-68-1 Acetic acid (2S,3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl ester 
• 81308-68-1 Acetic acid (2R,3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl ester 
• 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 highly efficient TEMPO mediated oxidation of sugar primary alcohols into uronic acids using 1-chloro-1,2-benziodoxol-3(1H)-one at room temperature

Oxidation of various sugar primary alcohols into corresponding uronic acids was demonstrated using 1-chloro-1,2-benziodoxol-3(1H)-one and TEMPO. The reaction proceeds at room temperature in good to excellent yields. Primary alcohols get oxidized selective

An approach to the synthesis of α-(1-6)-C-disaccharides by tandem Tebbe methylenation and Claisen rearrangement

Uronic acids, most efficiently synthesised from the corresponding alcohols by two step Dess-Martin and sodium chlorite mediated oxidation, may be used as coupling partners for esterification with an allo glycal as substrates for the tandem Tebbe/Claisen a

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.

REDUCTIVE ONE-STEP ELIMINATION OF AN ACETOXYL RESIDUE AT β-POSITION OF A NITRO GROUP: SYNTHESES OF (-)-SHIKIMIC ACID FROM D-MANNOSE AND 2-DEOXYSTREPTAMINE PENTAACETATE FROM N-ACETYL-D-GLUCOSAMINE

By utilizing a reductive one-step elimination reaction of an acetoxyl residue at β-position of the nitro group in cyclitols, a synthesis of the ketocyclitol triacetate (15a), which was already converted to (-)-shikimic acid (16) and (-)-guinic acid (17), from D-mannose (4) and a conversion from N-acetyl-D-glucosamine (18) to 2-deoxystreptamine pentaacetate (22) have been accomplished.