182212-07-3

Upstream product

• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 3458-28-4 D-Mannose 
• 107-18-6 allyl alcohol 
• 530-26-7 D-Mannose 
• 16754-50-0 triallyl orthoformate 
• 106-95-6 allyl bromide 
• 214490-84-3 Allyl 2,3,4,6-Tetra-O-acetyl-D-mannopyranoside 

Downstream Products

• 223123-44-2 allyl 6-O-tosyl-α-D-mannopyranoside 
• 289726-12-1 allyl 6-O-trityl-D-mannopyranoside 
• 1056479-53-8 allyl-4,6-O-benzylidene-2,3-di-O-hydroxy-D-mannopyranoside 
• 194594-76-8 (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 
• 119111-10-3 Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2R)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester 
• 20770-84-7 2,3-di-O-benzyl-4,6-O-benzylidene-α/β-D-mannopyranose 
• 119237-93-3 (R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-manno-hept-1-enitol 
• 60887-18-5 (2R,4aR,7S,8R,8aR)-6-Allyloxy-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 37111-83-4 (2R,4aR,7S,8S,8aS)-6-Allyloxy-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 119237-95-5 <2R-(2α,4aβ,5β,6β,7β,7aβ)>-Hexahydro-5-methyl-2-phenyl-6,7-bis(phenylmethoxy)cyclopenta-1,3-dioxin 
• 119237-94-4 <2R-(2α,4aβ,5α,6β,7β,7aβ)>-Hexahydro-5-methyl-2-phenyl-6,7-bis(phenylmethoxy)cyclopenta-1,3-dioxin 
• 92528-11-5 allyl 2,4,6-tri-O-acetyl-3-O-(3,6-dideoxy-2,4-di-O-p-nitrobenzoyl-β-D-xylo-hexopyranosyl)-α-D-mannopyranoside 
• 92528-10-4 allyl 2,4,6-tri-O-acetyl-3-O-(3,6-dideoxy-2,4-di-O-p-nitrobenzoyl-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside 
• 20746-71-8 Allyl 2,3-Bis-O-(phenylmethyl)-4,6-(phenylmethylene)-D-mannopyranoside 

Relevant academic research and scientific papers

Synthesis and affinities of C3-symmetric thioglycoside-containing trimannosides

Thioglycoside-containing trimannose analogs were designed and prepared to mimic the natural N-glycan core trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man. (1→6)-S-Linked trimannoside 1 and its trivalent cluster 2 were synthesized in 11 and 15 steps, respectively, taking advantages of the armed mannopyranosyl trichloroacetimidate as glycosyl donor. Hemagglutination inhibition of the two new thiomannotriose analogs was preliminarily examined. Comparing to the parent trimannoside α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man-OMe, the cluster mannotrioside 2 presented a comparable binding affinity to Con A, while the monomer 6-S-trimannoside 1 exhibited a slightly lower inhibition ability.

β-selective C-mannosylation of electron-rich phenols

The reaction of tetra-O-benzylmannosyl trichloroacetimidate with electron-rich phenols in the presence of TMSOTf surprisingly leads to the exclusive formation of aryl β-C-glycosides while a preference for the -anomer could be observed with other Lewis aci

Synthesis of benzaldehyde-functionalized glycans: A novel approach towards glyco-SAMs as a tool for surface plasmon resonance studies

In recent years the interest in tools for investigating carbohydrateprotein (CPI) and carbohydrate-carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self-assembled monolayers (SAM) of carbohydrate derivatives, which can mimic the glycocalyx. In contrast to the SPR imaging methods used previously to analyze CPI and CCI, the novel approach reported herein allows a facile and rapid synthesis of linker spacers and carbohydrate derivatives and enhances the binding event by controlling the amount and orientation of ligand. For immobilization on biorepulsive amino-functionalized SPR chips by reductive amination, diverse aldehyde-functionalized glycan structures (glucose, galactose, mannose, glucosamine, cellobiose, lactose, and lactosamine) have been synthesized in several facile steps that include olefin metathesis. Effective immobilization and the first binding studies are presented for the lectin concanavalin A.

Montmorillonite K-10 as a reusable catalyst for fischer type of glycosylation under microwave irradiation

Montmorillonite K-10-catalyzed Fischer type glycosylation was studied for various monosacharides with different alcohols under microwave irradiation. The method was found to be efficient, economic, simple, and time saving and the catalyst montmorillonite K-10 was reused three times without loss of catalytic activity and anomeric selectivity. With glycerol, the method gave products glycosylated at primary alcohols only.

Synthetic 3-O-methylmannose-containing polysaccharides (sMMPs): Design and synthesis

With the hope of mimicking the chemical and biological properties of natural 3-O-methylmannose-containing polysaccharides (MMPs), synthetic 3-O-methylmannose-containing polysaccharides (sMMPs) were designed and synthesized in a convergent manner. With lit

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.

Use of allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3-, C4-, and C5-carbon sources: Palladium-catalyzed allylation of aldehydes

Palladium-diethylzinc or palladium-triethylborane catalytically promotes self-allylation of 2-(allyloxy)tetrahydrofurans, 2-(allyloxy)tetrahydropyrans, and their hydroxy derivatives on the rings (ribose, glucose, mannose, deoxyribose, deoxyglucose). All the reactions proceed at room temperature and provide polyhydroxyl products, sharing a structural motif of a homoallyl alcohol, in good to excellent yields with high levels of stereoselectivity. Useful Crunit elongation, which makes the best use of an allyl ether as a protecting group and a nucleophilic allylation agent, is demonstrated. Mechanisms for the umpolung reaction (of an allyl ether into an allylic anion) and stereoselectivity associated with allylation of aldehydes are discussed.

Microwave-accelerated Fischer glycosylation

Fischer glycosylation has been used for decades for the synthesis of simple alkyl and aryl glycosides from free sugars. The reaction proceeds under reflux in the presence of catalytic acid with the alcohol as solvent. The main deficiency of this reaction is the long reaction time required. In this study microwave heating has been utilised for the Fischer glycosylation reaction of N-acetyl-d-glucosamine, N-acetyl-d-galactosamine, d-glucose, d-galactose and d-mannose with a variety of alcohols (methanol, ethanol, benzyl alcohol and allyl alcohol). Remarkable acceleration of the glycosylation reactions (minutes compared to hours) over conventional reflux heating was observed with good yields and production of the α-glycoside as the dominant product.

A practical synthetic method for α- and β-glycosyloxyacetic acids

Dihydroxylation of allyl 2,3,4-tri-O-benzyl-6-O-tritylglycosides provides diols, the anomers of which can easily be separated by column chromatography in a practical scale. These anomers can be cleanly transformed into α- and β-glycosyloxyacetic acids, respectively, via oxidative cleavage of the diol followed by oxidation.

Synthesis of sialyl Lewis x mimetics as selectin inhibitors by enzymatic aldol condensation reactions

Several D-mannosyl phosphate/phosphonate derivatives have been enzymatically prepared as sialyl Lewis x tetrasaccharide mimics, which showed strong-to-moderate inhibition against E-, P-, and L-selectins. The synthesis of these mimics is very straightforward; mannosyl aldehyde derivatives are condensed with dihydroxyacetone phosphate (DHAP) in the presence of a DHAP-dependent aldolase to provide mannosyl phosphates. Copyright (C) 1999 Elsevier Science Ltd.