117305-40-5

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 

Downstream Products

• 126836-22-4 (2R,4aR,6S,7R,8aR)-7-[(S)-Hydroxy-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methyl]-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 220864-58-4 methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside 
• 103597-18-8 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-α-D-glycero-D-gluco-octopyranoside 
• 103597-22-4 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside 
• 194724-39-5 (E)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-octa-5,7-dienal 
• 220886-36-2 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-7-C-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-galacto-hept-6-ynopyranoside 
• 220886-37-3 methyl 6-C-(2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-β-D-glycero-L-manno-heptitol-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranoside 
• 220864-60-8 6-C-(2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-β-D-glycero-L-manno-heptitol-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-D-galactono-1,5-lactone 

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.

Hydroxy-directed, SmI2-induced conversion of carbohydrates into carbocycles

Polyoxygenated six-membered carbocycles were derived from carbohydrates with complete stereocontrol through hydroxy-directed coupling cyclization induced by SmI2. For example, the cis-1,3-cyclohexanediol 3 is obtained from the D-glucopyranoside derivative 1 in excellent yield. The coupling cyclization is initiated by single-electron transfer from SmI2 to the formyl group of the δ-hydroxy aldehyde 2 generated in an equilibrium process.

Synthesis of vinyl- and alkynylcyclopentanetetraols by SmI2/Pd(0)-promoted carbohydrate ring-contraction

A variety of vinyl- or alkynyl-substituted polyhydroxylated cyclopentanes and cyclobutanes are prepared in enantiomerically pure form from appropriate carbohydrate precursors, in a direct one-step ring-contraction procedure promoted by SmI2 and catalytic Pd(0). This reaction is thought to proceed through intermediate ring-opened allyl- or allenylsamarium complexes that undergo ring-closure by intramolecular carbonyl addition. A predominant trans relationship is found between vinyl (or alkynyl) and hydroxyl groups at the two newly created stereogenic centers, with good to excellent levels of stereoselectivity being observed in the formation of homopropargyl cyclopentanol products. Under appropriate conditions, preparatively useful yields are realized of stereoisomers not directly available using alternative methodology.

Synthesis of C-oligosaccharides that mimic their natural O-analogous immunodeterminants in binding to monoclonal immunoglobulins

We have stereoselectively synthesized the analogues of the methyl β- glycosides of (1 → 6)-β-D-galacto-oligosaccharides (up to tetrasaccharide), in which the interglycosidic oxygen atoms are replaced by a methylene group.

FROM SUGAR ALLYLTIN DERIVATIVES TO CHIRAL DIENOALDEHYDES AND TRIENOATES

Sugar dialdoses 5, 9, 15, and 16 were converted into allyltin derivatives 4, 12, 13, and 14, in yields of 35 - 47percent respectively.Treatment of 4, 12, and 13 with a mild Lewis acid (ZnCl2) in methylene chloride caused rearrangement to appropriate dieno

Diastereoselectivity in the synthesis of D-glycero-D-aldoheptoses by 2-trimethylsilylthiazole homologation from hexodialdo-1,5-pyranose derivatives

An exploration of the synthesis of D-glycero-D-altro-heptose, a constitutent of O antigen chains in lipopolysaccharides from Campylobacter jejuni serotypes O:23 and O:36 led to a study of the 2-trimethylsilylthiazole homologation procedure for heptose syn