103703-00-0

Upstream product

• 10230-17-8 O³-benzyl-D-glucose 
• 108-24-7 acetic anhydride 
• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 97590-76-6 benzyl-O-β-D-glucopyranoside 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 492-62-6 alpha-D-glucopyranose 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 100-39-0 benzyl bromide 
• 127-09-3 sodium acetate 
• 42926-91-0 3-O-benzyl-1,6-anhydro-β-L-idopyranose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 100-44-7 benzyl chloride 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 39708-09-3 methyl-(O³-benzyl-O²,O⁴,O⁶-trimethyl-ξ-D-glucopyranoside) 
• 124813-93-0 benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 87791-22-8 1-O-Acetyl-3-O-benzyl-2,4,6-tri-O-methyl-β-D-glucopyranose 
• 87791-21-7 1-O-Acetyl-3-O-benzyl-2,4,6-tri-O-methyl-α-D-glucopyranose 
• 80064-96-6 N⁴-acetyl-1-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)cytosine 
• 124813-99-6 methyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 124814-09-1 C₈₀H₈₆O₁₉ 
• 146530-62-3 ethyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 22331-16-4 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 
• 22331-15-3 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranoside 
• 103082-79-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-glucopyranose 
• 158198-55-1 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 34339-69-0 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide 
• 180072-37-1 2,3,4-tri-O-acetyl-6-O-benzylglucosyl bromide 

Relevant academic research and scientific papers

Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.

Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound

The invention discloses discloses synthesis of a helicobacter-pylorus O2 serotype O antigen oligosaccharide compound, and belongs to the field of organic synthesis. According to the synthesis, helicobacter-pylorus O2 serotype O-antigen disaccharide to tet

Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative

The invention discloses a preparation method of a clostridium bolteae surface capsular polysaccharide structure derivative and belongs to the field of sugar chemistry. The preparation method comprisesthe following steps: taking glucose as a glycosyl donor to obtain a target beta-glycosidic bond; then successfully synthesizing a disaccharide building block through an oxidization-reduction glucoseC-2 site method; then synthesizing a target oligosaccharide structure which takes the disaccharide building block as a repeating unit, such as the gram-positive bacterium surface capsular polysaccharide structure derivative [arrow3]-alpha-D-Manp-(1arrow4)-beta-D-Rhap-(1arrow]5-Linker. A reducing end of decaose is connected with a connecting arm and is used for connecting protein to form a glycoconjugate for carrying out immunology researches. The method provided by the invention has the advantages of simplicity, time saving, labor saving and low cost; the obtained clostridium bolteae surface capsular polysaccharide structure derivative is possibly used for developing and preparing medicine related to autism.

Glycosylations of Simple Acceptors with 2-O-Acyl l-Idose or l-Iduronic Acid Donors Reveal Only a Minor Role for Neighbouring-Group Participation

Several l-idose and l-iduronic acid glycosyl donors (mostly thioglycosides but also halides and trichloroacetimidates) with acyl protecting groups at the C-2 position were prepared and evaluated in glycosylation reactions with simple acceptors. In glycosaminoglycan oligosaccharide syntheses in the literature, the presence of C-2 acyl protecting groups in l-ido-configured glycosyl donors generally results in exclusive formation of 1,2-trans glycosidic linkages, a finding that has typically been attributed to neighbouring-group participation. However, glycosylations of simple alcohols with l-ido-configured donors (particularly thioglycosides), reported here, generally displayed incomplete stereocontrol and gave mixtures of the 1,2-trans and 1,2-cis products, suggesting that neighbouring-group participation has lesser importance in these reactions. Glycosyl donors and reaction conditions were identified that gave improved, but not exclusive, selectivity for the desired α-l-anomer (1,2-trans) as the major product. Interestingly, glycosylations under the same reaction conditions with more complex monosaccharide acceptors gave exclusively the expected 1,2-trans products. The role of neighbouring-group participation in these glycosylations was explored with density functional theory (DFT) calculations, which revealed that the non-stereoselective addition of the acceptor alcohol to the intermediate oxocarbenium ion is competitive with the stereospecific addition of the acceptor to the acyloxonium ion intermediate.

Total synthesis of viscumneoside III of Viscum coloratum

The first total synthesis of viscumneoside III, a promising anti-angina pectoris dihydroflavone O-glycoside isolated from Viscum coloratum was described here. Trichloroaceti-midate was employed as the apiofuranosyl donor to construct the key building block of homoeriodictyol-7-O-β-D-apiosyl-(1 → 2)-β-D-glycoside (1). The longest linear sequence (from 2 to 1) in the synthetic route required thirteen steps and afforded the final product 1 with an overall yield of 6.3%.

Automated glycan assembly of a s. pneumoniae serotype 3 cps antigen

Vaccines against S. pneumoniae, one of the most prevalent bacterial infections causing severe disease, rely on isolated capsular polysaccharide (CPS) that are conjugated to proteins. Such isolates contain a heterogeneous oligosaccharide mixture of differe

Azetidine iminosugars from the cyclization of 3,5-Di- O -triflates of α-furanosides and of 2,4-Di- O -triflates of β-pyranosides derived from glucose

Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.

Multi-gram synthesis of a hyaluronic acid subunit and synthesis of fully protected oligomers

Fully protected tetra-, hexa- and octasaccharides of hyaluronic acid were synthesized on a scale of several 100 mg up to gram quantities using allyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)- (1→3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D- glucopyranoside as a key building block. This disaccharide was subjected to deprotection, then glycosylation via the trichloroacetimidate method was employed to achieve the formation of the oligosaccharides.

The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?

The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.

First Synthesis of a Trisaccharide of Glycosylkaemferide: A Resistance Factor in Carnations

A trisaccharide, phenyl β-D-glucopyranosyl-(1→2)-[α -L-rhamnopyranosyl-(1→6)]-1-thio-β-D-glucopyranoside, of glycosylkaemferide, a resistance factor in carnations, was synthesized in a practical way.