138181-68-7

Upstream product

• 67-56-1 methanol 
• 350985-71-6 phenyl 3,4,6-tri-O-benzyl-2-O-(1-para-methoxyphenylethenyl)-1-thio-β-D-glucopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 4670-62-6 tetra-N-butylammonium benzenethiolate 
• 108-98-5 thiophenol 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 250273-77-9 1,2-Di-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 350985-70-5 phenyl 3,4,6-tri-O-benzyl-2-O-para-methoxybenzoyl-1-thio-β-D-glucopyranoside 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 100-39-0 benzyl bromide 
• 211947-53-4 (2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(phenylthio)tetrahydro-2H-pyran-3-yl benzoate 

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 
• 350985-70-5 phenyl 3,4,6-tri-O-benzyl-2-O-para-methoxybenzoyl-1-thio-β-D-glucopyranoside 
• 1169827-75-1 phenyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-1-thio-β-D-glucopyranoside 
• 205987-04-8 methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside S5 
• 1180492-20-9 phenyl 2-O-[((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)dimethylsilane]-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

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

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

Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation

In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra

Stereoselective synthesis of α-glucosides by neighbouring group participation via an intermediate thiophenium ion

The use of a 2-O-(thiophen-2-yl)methyl protecting group allows highly stereoselective α-glucosylation of a trichloroacetimidate donor; increased stereoselectivity, presumably arising from the intramolecular formation of a transient intermediate thiophenium ion, correlates with increased bulk of the glycosyl acceptor.

PROCESS FOR PRODUCING 1,2-TRANS-GLYCOSIDE COMPOUND

In preparing a glycoside compound from (a) a furanose compound or pyranose compound, and (b) an alcohol compound, a process for preparing a glycoside compound in which glycosidic bond locates selectively trans form relative to C-2 hydroxyl group, the proc

Single-step multisyntheses of glycosyl acceptors: Benzylation of n-1 hydroxyl groups of phenylthio glycosides of xylose, mannose, glucose, galactose, 2-azido-2-deoxy-glucose, and 2-azido-2-deoxy-galactose

An array of synthons is required to access an oligosaccharide library; however, multistep and thus time-consuming synthesis is inevitable. To rapidly access such synthetic units, multiple benzylation reactions of monosaccharides under phase-transfer condi