159353-70-5

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 158716-07-5 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 159407-19-9 phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 108-98-5 thiophenol 
• 67-56-1 methanol 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 83-87-4 D-Mannose pentaacetate 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 168138-13-4 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-hydroxy-3-butenyl>-2-phenyl-1,3-dioxane 
• 168138-12-3 (2R,4S)-4-[(1R,2R)-1-Benzyloxy-2-(4-methoxy-benzyloxy)-but-3-enyl]-2-phenyl-[1,3]dioxan-5-one 
• 172967-72-5 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane 
• 168138-11-2 (1'R,2R,2'R,4R,5R)-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-5-hydroxy-2-phenyl-1,3-dioxane 
• 168254-34-0 (1'R,2R,2'R,4R,5S)-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-5-hydroxy-2-phenyl-1,3-dioxane 
• 168138-21-4 (1'R,2R,2'R,4R,5S)-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-5-hydroxy-2-phenyl-1,3-dioxane 
• 168138-20-3 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane 
• 1443672-37-4 benzyl 3-O-benzyl-4,6-O-benzylidene-2-O-p-methoxybenzyl-β-D-mannopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside 
• 1418269-48-3 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-mannitol-1-yl 3-O-benzyl-4,6-O-benzylidene-2-O-octanoyl-β-D-mannopyranoside 
• 1418269-47-2 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-mannitol-1-yl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 1418269-46-1 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-mannitol-1-yl 3-O-benzyl-4,6-O-benzylidene-2-O-p-methoxybenzyl-β-D-mannopyranoside 
• 1380489-88-2 2-azidoethyl (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 1380489-87-1 2-azidoethyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 

Relevant academic research and scientific papers

P-chlorobenzyl ether: A p-methoxybenzyl ether in disguise

In the chemistry of polyfunctionalized organic compounds, protecting groups that can undergo mild and selective cleavage while still being stable during the entire synthetic sequence are often required. In this work, we present a straightforward conversion of the robust p-chlorobenzyl ether into the more labile and well-described p-methoxybenzyl ether using palladium catalysis. This reaction was demonstrated to be high yielding and compatible with a wide range of functionalities, thereby providing a useful supplement to the conventional ether protecting groups.

Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides

Phosphorylated β-(1→2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated β-(1→2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group.

The first total synthesis of acremomannolipin A, the potential Ca 2+ signal modulator with a characteristic glycolipid structure, isolated from the filamentous fungus Acremonium strictum

The first total synthesis of acremomannolipin A, the potential Ca 2+ signal modulator isolated from Acremonium strictum, was achieved by employing the characteristic stereoselective β-mannosylation of 4,6-O-benzylidene-protected mannosyl sulfox

Stereoselective total synthesis of acremomannolipin A and its anomer, the potent calcium signal modulators with a novel glycolipid structure: Role of the stereochemistry at the anomeric center on the activity

A full account of stereoselective total synthesis of a novel glycolipid, acremomannolipin A (1), the potent calcium signal modulator isolated from Acremonium strictum, by employing the stereoselective β-mannosylation of 4,6-O-benzylidene-protected mannosy

Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: Sugar moiety of antitumor antibiotic bleomycin

A new route to the disaccharide moiety (2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose) of the antitumor agent bleomycin was developed. Both the L-gulose synthon 21 and the 3-O-carbamoyl-D-mannose segment 30 were prepared from D-mannose in a regioselective manner by applying stannylene acetal methodology. Glycosylation of 21 with 30 proceeded smoothly, and further conversion to disaccharide derivatives (33 and 34) was successfully accomplished.

Preparation of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: Synthetic study on the sugar moiety of antitumor antibiotic bleomycin

A new practical route to the disaccharide moiety of bleomycin was developed. Both of key building blocks 9 and 16 were prepared from D-mannose in a regioselective manner by applying stannylene acetal methodology. Glycosylation of the allyl alcohol 9 with the trichloroacetimidate 16 proceeded smoothly, and the further incorporation to the disaccharide moiety was succesfully accomplished.

New method for the preparation of L-gulose from D-mannose: Synthetic study on the sugar moiety of bleomycin

L-gulose, a key building block of the carbohydrate moiety of antitumor antibiotic bleomycins, is prepared from D-mannose by the inversion at C-5.