13350-45-3

Usage

Uses

Used in Pharmaceutical Applications:
METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOGLUCOPYRANOSIDE is used as a synthetic intermediate for the development of pharmaceutical compounds. Its potent reactivity and the presence of a sulfide group in its structure make it a valuable component in the synthesis of various drugs.
Used in Synthetic Chemistry:
METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOGLUCOPYRANOSIDE is used as a synthetic intermediate in the field of synthetic chemistry. Its acetyl groups and sulfide part contribute to its reactivity, allowing for the creation of a wide range of chemical compounds.

InChI:InChI=1/C15H22O9S/c1-7(16)20-6-11-12(21-8(2)17)13(22-9(3)18)14(23-10(4)19)15(24-11)25-5/h11-15H,6H2,1-5H3/t11-,12-,13+,14-,15+/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 74-88-4 methyl iodide 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 83-87-4 D-glucose pentaacetate 
• 17314-32-8 tributyl(methylthio)stannane 
• 917-64-6 methyl magnesium iodide 
• 127066-70-0 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate 
• 108-24-7 acetic anhydride 
• 30760-09-9 methyl 1-deoxy-1-thio-β-D-glucopyranoside 
• 19879-84-6 tetraacetyl thioglucose 
• 3908-55-2 Trimethyl(methylthio)silane 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 74808-17-6 methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 3180-75-4 1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-N-acetyl-cytosin 
• 3624-39-3 tetra-O-acetyl-1-(6-benzoylamino-purin-9-yl)-β-D-1-deoxy-glucopyranose 
• 82231-38-7 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 54165-55-8 (3R)-3-Acetoxy-β-ionon 
• 71423-43-3 (E)-3,5,5-trimethyl-4-(3-oxobut-1-en-1-yl)cyclohex-3-en-1-yl acetate 
• 710281-93-9 benzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-(3,4-O-isopropylidene)-α-L-arabinopyranoside 
• 710282-01-2 benzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3-O-(4-methoxybenzyl)-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-L-arabinopyranoside 
• 710281-98-4 benzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-O-acetyl-3-O-(4-methoxybenzyl)-α-L-arabinopyranoside 
• 854735-94-7 methyl 4,6-O-cyclohexylidene-2,3-di-O-(benzyl-d7)-1-thio-β-D-glucopyranoside 
• 854735-99-2 methyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 
• 114967-51-0 isopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of Branched Tetrasaccharide Derivatives of Schizophyllan-like β-Glucan

Branched tetrasaccharide derivatives as the repeating units of schizophyllan were synthesized using a common intermediate that had different protecting groups on the hydroxyl groups. Accordingly, β-1,3-disaccharide acceptors were efficiently glycosylated

Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.

Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates

A mild organophotoredox synthetic protocol for forming a Csp3-S/Se bond by reacting widespread redox-active esters with thio/selenosulfonates has been developed. The power of the synthetic manifold is fueled by an unprecedented broad substrate scope and wide functional group tolerance.

Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy

While strategies involving a 2e- transfer pathway have dictated glycosylation development, the direct glycosylation of readily accessible glycosyl donors as radical precursors is particularly appealing because of high radical anomeric selectivity and atom- and step-economy. However, the development of the radical process has been challenging owing to notorious competing reduction, elimination and/or SN side reactions of commonly used, labile glycosyl donors. Here we introduce an organophotocatalytic strategy through which glycosyl bromides can be efficiently converted into corresponding anomeric radicals by photoredox mediated HAT catalysis without a transition metal or a directing group and achieve highly anomeric selectivity. The power of this platform has been demonstrated by the mild reaction conditions enabling the synthesis of challenging α-1,2-cis-thioglycosides, the tolerance of various functional groups and the broad substrate scope for both common pentoses and hexoses. Furthermore, this general approach is compatible with both sp2 and sp3 sulfur electrophiles and late-stage glycodiversification for a total of 50 substrates probed.

Synthesis of O-1- O-6 Substituted Positional Isomers of d -Glucose-Thioether Ligands and Their Ruthenium Polypyridyl Conjugates

A library of positional isomers of d-glucose (O-1-O-6) as ligands and their 11 light-active ruthenium conjugates has been synthesized. A protecting group strategy without the necessity of using palladium on carbon for the modification for the 2-O and 4-O position allows for the incorporation of sulfur donor atoms as ligands for transition metal complexes.

Interrupted Pummerer Reaction in Latent-Active Glycosylation: Glycosyl Donors with a Recyclable and Regenerative Leaving Group

Latent O-glycosides, 2-(2-propylthiol)benzyl (PTB) glycosides, were converted into the corresponding active glycosyl donors, 2-(2-propylsulfinyl)benzyl (PSB) glycosides, by a simple and efficient oxidation. Treatment of the PSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. The leaving group, which was activated by an interrupted Pummerer reaction, can be recycled (PSB-OH) and regenerated as the precursor (PTB-OH). A natural hepatoprotective glycoside, leonoside F, was efficiently synthesized in a convergent [3+1] manner with this newly developed method. The present total synthesis also led to a structural revision of this phenylethanoid glycoside.

Acyl transfer reactions of carbohydrates, alcohols, phenols, thiols and thiophenols under green reaction conditions

Acyl transfer reactions of various carbohydrates, alcohols, phenols, thiols and thiophenols were achieved at room temperature in high yields and catalytic efficiency in the presence of methane sulfonic acid, a green organic acid, under solvent-free conditions over short time periods. The method is mild enough to allow acid labile substituents such as isopropylidene acetals and trityl ethers on the reacting substrates to be left completely unaffected. Esterification of free mono- and dicarboxylic acids such as acetic acid, cinnamic acid, sialic acid and tartaric acid with alcohols such as menthol, ethanol, methanol or propylene glycol has also been achieved efficiently at room temperature. A comparative study of the method with the silica-sulfuric acid is also reported.

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.

Synthetic studies on pterin glycosides: the first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin

l-Rhamnose was led, in a 14-step-sequence, to N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2′-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methox

First synthesis of biopterin α-D-glucoside

A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α- D-glucopyranosy bromide (15) was efficiently prepared from D-glucose in 8 steps. The first synthesis of 2'-O-(α-D-glucopyranosyl)biopterin (2) was achieved by treatment of the key precursor, N2-(N,N- dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl] biopterin (6) with 15 in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.