148968-90-5

Upstream product

• 71672-07-6 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 99388-26-8 benzyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 115969-50-1 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 183064-37-1 phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 33106-26-2 2-benzyloxypropanol 
• 88567-59-3 phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 5328-50-7 D-cellobiose octaacetate 
• 146774-41-6 2-methoxyethyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 84396-49-6 allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1[*]4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 27891-73-2 β-phenylsulfanyl lactoside 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 
• 126777-85-3 2-methoxyethyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 

Downstream Products

• 83921-72-6 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 83921-71-5 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 144946-83-8 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-D-glucose oxime 
• 149300-00-5 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranosyl fluoride 
• 173325-23-0 1-O-acetyl-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-D-glucopyranose 
• 171412-15-0 allyl O-(2,3,4-tri-O-benzyl-6-O-p-nitrobenzenesulfonyl-α-D-glucopyranosyl)-(1<*>6)-O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 171411-96-4 allyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 144946-82-7 2,2',3,3',4',6,6'-hepta-O-benzyl-N-hydroxy-D-maltonimido-1,4-lactone 
• 139172-73-9 2,2',3,3',4',6,6'-hepta-O-benzyl-N-(<1'',2''-bis(methoxycarbonyl)vinyl>oxy)-D-maltonimido-1,4-lactone 
• 1562507-65-6 3,4,7-tri-O-benyl-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-D-glucphept-1-enitol 
• 1562507-92-9 dibenzyl 2,3,6,2',3',4',6'hepta-O-benzyl-α-D-maltosyl phosphate 

Relevant academic research and scientific papers

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bioorganic chemistry and medicinal chemistry, yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation–reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on commercial disaccharides, as shown in four examples, as well as on disaccharides that are not commercially available and are synthesized for this purpose, as shown by a fifth example.

Synthesis of a C-phosphonate mimic of maltose-1-phosphate and inhibition studies on Mycobacterium tuberculosis GlgE

The emergence of extensively drug-resistant tuberculosis (XDR-TB) necessitates the need to identify new anti-tuberculosis drug targets as well as to better understand essential biosynthetic pathways. GlgE is a Mycobacterium tuberculosis (Mtb) encoded maltosyltransferase involved in α-glucan biosynthesis. Deletion of GlgE in Mtb results in the accumulation of M1P within cells leading to rapid death of the organism. To inhibit GlgE a maltose-C-phosphonate (MCP) 13 was designed to act as an isosteric non-hydrolysable mimic of M1P. MCP 13, the only known inhibitor of Mtb GlgE, was successfully synthesized using a Wittig olefination as a key step in transforming maltose to the desired product. MCP 13 inhibited Mtb GlgE with an IC50 = 230 ± 24 μM determined using a coupled enzyme assay which measures orthophosphate release. The requirement of M1P for the assay necessitated the development of an expedited synthetic route to M1P from an intermediate used in the MCP 13 synthesis. In conclusion, we designed a substrate analogue of M1P that is the first to exhibit Mtb GlgE inhibition.

C-Glycosyl amino acids through hydroboration-cross-coupling of exo-glycals and their application in automated solid-phase synthesis

O-Glycosylation is one of the most important post-translational modifications of proteins. The attachment of carbohydrates to the peptide backbone influences the conformation as well as the solubility of the conjugates and can even be essential for binding to specific ligands in cell-cell interactions or for active transport over membranes. This makes glycopeptides an interesting class of compounds for medical applications. To enhance the long-term availability of these molecules in vivo, the stabilization of the glycosidic bond between the amino acid residue and the carbohydrate is of interest. The described modular approach affords β-linked C-glycosyl amino acids by a sequence of Petasis olefination of glyconolactones, stereoselective hydroboration and a mild B-alkyl-Suzuki coupling reaction. The coupling products were transformed to C-glycosyl amino acid building-blocks suitable for solid-phase synthesis and successfully incorporated into a partial sequence of the tumor-associated MUC1-glycopeptide. The resulting C-glycopeptides are candidates for the development of long-term stable mimics of O-glycopeptide vaccines. Copyright

Convergent synthesis of homogeneous Glc1Man 9GlcNAc2-protein and derivatives as ligands of molecular chaperones in protein quality control

A detailed understanding of the molecular mechanism of chaperone-assisted protein quality control is often hampered by the lack of well-defined homogeneous glycoprotein probes. We describe here a highly convergent chemoenzymatic synthesis of the monoglucosylated glycoforms of bovine ribonuclease (RNase) as specific ligands of lectin-like chaperones calnexin (CNX) and calreticulin (CRT) that are known to recognize the monoglucosylated high-mannose oligosaccharide component of glycoproteins in protein folding. The synthesis of a selectively modified glycoform Gal1Glc 1Man9GlcNAc2-RNase was accomplished by chemical synthesis of a large N-glycan oxazoline and its subsequent enzymatic ligation to GlcNAc-RNase under the catalysis of a glycosynthase. Selective removal of the terminal galactose by a β-galactosidase gave the Glc1Man 9GlcNAc2-RNase glycoform in excellent yield. CD spectroscopic analysis and RNA-hydrolyzing assay indicated that the synthetic RNase glycoforms maintained essentially the same global conformations and were fully active as the natural bovine ribonuclease B. SPR binding studies revealed that the Glc1Man9GlcNAc2-RNase had high affinity to lectin CRT, while the synthetic Man9GlcNAc 2-RNase glycoform and natural RNase B did not show CRT-binding activity. These results confirmed the essential role of the glucose moiety in the chaperone molecular recognition. Interestingly, the galactose-masked glycoform Gal1Glc1Man9GlcNAc2-RNase also showed significant affinity to lectin CRT, suggesting that a galactose β-1,4-linked to the key glucose moiety does not significantly block the lectin binding. These synthetic homogeneous glycoprotein probes should be valuable for a detailed mechanistic study on how molecular chaperones work in concert to distinguish between misfolded and folded glycoproteins in the protein quality control cycle.

OLIGOSACCHARIDE DERIVATIVE

Compounds having the formula (I) : (wherein, A represents a group such as a cyclic group, R1 and R2 represent groups such as alkyl groups or hydroxymethyl groups, and n represents 1 or 2), or pharmacologically acceptable salts thereo

A new efficient method for catalytic hydrolysis of thioglycoside

A new and efficient method for catalytic hydrolysis of thioglycosides was successfully developed. Various thioglycosides were smoothly hydrolyzed to afford the corresponding 1-hydroxy sugars in high yields. The hydrolysis of disaccharides was took place smoothly without accompanying no anomerization of existing glycosidic bond.

Synthesis of α,α-, α,β-, and β,β-(dimaltoside)s of ethane-1,2-diol, propane-1,3-diol, and butane-1,4-diol: A proposal for an initial adhesion mode

Nine dimaltoside derivatives of ethane-1,2-diol, propane-1,3-diol, and butane-1,4-diol having the α,α, α,β, and β,β anomeric configurations at the linkage sites have been synthesized. Suitably protected maltosyl halides or a 1-(phenylthio) derivative were condensed with the foregoing diols and the resulting monomaltosyl derivatives were further condensed with the maltosyl donors to give, after deprotection, the title compounds. Their structures were fully characterized by NMR spectroscopy. Interactions between the three α,α-(dimaltoside)s and cinnamyl alcohol are briefly discussed. Copyright (C) 1997 Elsevier Science Ltd.

Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose

Dehydrative glycosylations of the 2-, 3-, 4-, and 6-OH groups of D-glucopyranose with hepta-O-benzyl derivatives of glucobioses (O-D-glucopyranosyl-(1->n)-D-glucopyranose; n = 2, 3, 4, or 6) and lactose, in the presence of a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine in dichloromethane showed that the selectivity of the reaction depended on the anomeric configuration and the linking position to the reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated.The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1->2)-linked biosyl donor undergo α-condensation.Several new linear trisaccharides were obtained via debenzylation of the condensates.

Thermal Rearrangement of Alkyl O-Vinylcarbohydroximates to 2-Alkyloxazoles

Alkyl O-vinylcarbohydroximates, lactoxime O-vinyl ethers, and sugar lactoxime O-vinyl ethers undergo a novel thermal rearrangement to afford the corresponding 2-alkyloxazoles, 2-(ω-hydroxyalkyl)oxazoles, and oxazoles bearing a sugar moiety, respectively.This rearrangement can also occur under photochemical conditions.