127299-77-8

Upstream product

• 930-69-8 sodium thiophenolate 
• 211947-53-4 (2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(phenylthio)tetrahydro-2H-pyran-3-yl benzoate 
• 67-56-1 methanol 
• 350985-71-6 phenyl 3,4,6-tri-O-benzyl-2-O-(1-para-methoxyphenylethenyl)-1-thio-β-D-glucopyranoside 
• 250273-77-9 1,2-Di-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 2873-29-2 D-glucal triacetate 
• 100-39-0 benzyl bromide 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 882-33-7 diphenyldisulfane 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 138181-67-6 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 108-98-5 thiophenol 
• 68681-00-5 3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose 

Downstream Products

• 191216-55-4 Succinic acid mono-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl) ester 
• 152871-97-1 3,4,6-Tri-O-benzyl-β-D-glucopyranosyl phenyl sulfone 
• 256351-18-5 2-Methyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 328937-68-4 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid 
• 328937-70-8 3-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid 
• 191216-63-4 Succinic acid (2R,3S,4R,5R,6S)-5-acetylamino-4-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 191216-57-6 Succinic acid (2S,3R,4S,5R,6R)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 191216-69-0 Succinic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 191216-67-8 Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 1180492-11-8 phenyl 2-O-dimethylsilane-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Chemoenzymatic glycan-selective remodeling of a therapeutic lysosomal enzyme with high-affinity M6P-glycan ligands. Enzyme substrate specificity is the name of the game

Functionalization of therapeutic lysosomal enzymes with mannose-6-phosphate (M6P) glycan ligands represents a major strategy for enhancing the cation-independent M6P receptor (CI-MPR)-mediated cellular uptake, thus improving the overall therapeutic effica

C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups

The stereoselective introduction of the glycosidic bond is one of the main challenges in chemical oligosaccharide synthesis. Stereoselective glycosylation can be achieved using neighbouring group participation of a C-2 auxiliary or using additives, for example. Both methods aim to generate a defined reactive intermediate that reacts in a stereoselective manner with alcohol nucleophiles. This inspired us to develop new C-2 auxiliaries based on commonly used additive functionalities such as ethers, phosphine oxides and tertiary amides. Good 1,2-trans-selectivity was observed for the phosphine oxide and amide-based auxiliaries expanding the toolbox with new auxiliaries for stereoselective glycosylation reactions.

α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation

Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.

Dissection of the effects that govern thioglucoside and thiomannoside reactivity

Neighboring group effects were investigated in gluco- and manno-configured thioglycosides under NIS/TfOH activation. Donors possessing a 2-O-benzoyl group that are capable (1,2-trans) and incapable (1,2-cis) of exerting nucleophilic push were compared wit

Application of 2-substituted benzyl groups in stereoselective glycosylation

The use of 2-O-(2-nitrobenzyl) and 2-O-(2-cyanobenzyl) groups controls stereoselective formation of 1,2-trans-glycosidic linkages via the arming participation effect. The observed stereoselectivity likely arises from the intramolecular formation of cyclic intermediate between the electron-rich substituent and the donor oxacarbenium ion providing the expected facial selectivity for attack of the glycoside acceptor. The stereodirecting effect of the 2-nitro- and 2-cyanobenzyl groups attached at the remote position (C-3, C-4, and C-6) of the donor molecule have also been investigated. To prove the postulated mechanism based on the participation effect of 2-substituted benzyl groups in the glycosylation stereoselectivity we used DFT theoretical calculation methodology.

Intramolecular aglycon delivery for (1 → 2)-β-mannosylation: Towards the synthesis of phospholipomannan of Candida albicans

A high yielding method for 1,2-cis-β-D-mannosylation by intra-molecular aglycon delivery (IAD) through p-methoxy benzyl ether/acetal exchange and phenylsulfoxide donor is reported, along with its application in iterative assembly of antigenic (1 → 2)-β-pe

Chemical synthesis of asparagine-linked archaeal N-glycan from Methanothermus fervidus

Several N-linked glycoproteins have been identified in archaea and there is growing evidence that the N-glycan is involved in survival and functioning of archaea in extreme conditions. Chemical synthesis of the archaeal N-glycans represents a crucial step

Application of the 2-nitrobenzyl group in glycosylation reactions: A valuable example of an arming participating group

The application of the o-nitrobenzyl (oNBn) group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. This new ether-type arming group can broadly extend the concept of the use of participating groups in glycosylation reactions. Easy protection and deprotection of the oNBn group further confirms its usefulness in synthesis. The application of o-nitrobenzyl (oNBn) ether as an arming participating group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. Copyright

Synthesis of tri- and tetra-mannosides based on sequential one-pot three-component glycosylation reactions

Expeditious syntheses of tri- and tetra-mannosides were carried out based on sequential one-pot glycosylation strategy. In both of these syntheses TMSOTf activated trichloroacetimidate, the first glycosyl donor, and inexpensive readily accessible trichlor

Synthetic oligosaccharides as tools to demonstrate cross-reactivity between polysaccharide antigens

Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colitis, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide