55722-49-1

Usage

Uses

Used in Biochemical and Pharmaceutical Research:
Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside is used as a reagent in the synthesis of complex carbohydrates and glycoconjugates for various applications in biochemical and pharmaceutical research. Its unique structure allows for the creation of diverse carbohydrate-based compounds with potential therapeutic and diagnostic properties.
Used in Drug Development:
In the Pharmaceutical Industry, Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside is used as a key intermediate in the development of drugs targeting carbohydrate structures. Its ability to form glycoconjugates with various biologically active molecules enables the design of drugs with improved efficacy and selectivity.
Used in Vaccine Development:
In the Vaccine Industry, Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside is used as a component in the design and synthesis of carbohydrate-based vaccines. Its reactivity and structural versatility allow for the creation of vaccines that can specifically target pathogens with unique carbohydrate structures, potentially leading to more effective and targeted immunization strategies.
Used in Diagnostics:
In the Diagnostics Industry, Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside is used in the development of diagnostic tools that rely on the recognition and binding of carbohydrate structures. Its ability to form stable glycoconjugates with various detection agents, such as fluorescent dyes or enzymes, enables the creation of highly sensitive and specific diagnostic assays for detecting diseases and monitoring treatment responses.
Used in Studying Biological Processes:
Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside serves as a valuable tool in the exploration of biological processes involving carbohydrates and glycoconjugates. Its unique structure allows researchers to investigate the roles of carbohydrates in cellular recognition, signaling, and communication, as well as their involvement in various diseases and disorders. This knowledge can contribute to a better understanding of the underlying mechanisms of these processes and aid in the development of novel therapeutic strategies.

Upstream product

• 75-08-1 ethanethiol 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 23716-85-0 tri-n-butyltin(SC₂H₅) 
• 83-87-4 D-Mannose pentaacetate 
• 108-24-7 acetic anhydride 
• 7647-01-0 hydrogenchloride 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl iodide 
• 530-26-7 D-Mannose 
• 75-03-6 ethyl iodide 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 145259-92-3 C₃₄H₅₀O₈SSi₂ 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 117252-67-2 2-(Trimethylsilyl)ethyl-<2,3,4,6-tetra-O-acetyl-α-D-mannopyranosid> 
• 638188-78-0 8-azidooctyl 5-O-{3,4,6-tri-O-benzyl-2-O-[3,4,6-tri-O-benzyl-2-O-(α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl}-2,3-di-O-benzyl-β-D-arabinofuranoside 
• 482576-72-7 N-(9-fluorenylmethoxycarbonyl)-O-[O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->2)-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)]-L-threonine benzyl ester 
• 1039749-33-1 methyl S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-[O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)]-2,4-di-O-benzyl-α-D-mannopyranoside 
• 212192-83-1 ethyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 187152-88-1 ethyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 129750-23-8 Ethyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 71526-33-5 methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 116113-70-3 isopropyl-O-2,3,4,6-tetra-O-benzyl-β-D-mannopyranose 

Relevant academic research and scientific papers

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof

The invention discloses a beta-D-glucose short-chain fatty acid ester compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The compound is a compound shown as a formula I, or a stereoisomer, a pharmaceutically acceptable salt, a solvate or a prodrug of the compound shown as the formula I. The formula is as shown in the description, wherein R is a methyl group, an ethyl group, a propyl group, a propylene group, an isopropylidene group, a butyl group, a butylidene group, an isobutylidene group, an amyl group, a pentylidene group or an isoamylidene group. The compound has potential prevention and treatment effects on diabetes, hyperlipidemia, atherosclerosis, Alzheimer's disease, cardiovascular and cerebrovascular diseases,inflammation, tumors and depression.

A versatile approach to the synthesis of glycans containing mannuronic acid residues

Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linkedviaβ-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.

A versatile approach to the synthesis of mannosamine glycosides

O-Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O-picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3-O-benzoyl group. This journal is

Chemical glucosylation of pyridoxine

The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.

Developing a library of mannose-based mono-and disaccharides: A general chemoenzymatic approach to monohydroxylated building blocks

Regioselective deprotection of acetylated mannose-based mono-and disaccharides differently functionalized in anomeric position was achieved by enzymatic hydrolysis. Candida rugosa lipase (CRL) and Bacillus pumilus acetyl xylan esterase (AXE) were immobilized on octyl-Sepharose and glyoxyl-agarose, respectively. The regioselectivity of the biocatalysts was affected by the sugar structure and functionalization in anomeric position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monohydroxylated building blocks that could be used as intermediates for the synthesis of mannosylated glycoconjugate vaccines targeting mannose receptors of antigen presenting cells.

Triflic acid-mediated synthesis of thioglycosides

An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

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.

An Empirical Understanding of the Glycosylation Reaction

Reliable glycosylation reactions that allow for the stereo- and regioselective installation of glycosidic linkages are paramount to the chemical synthesis of glycan chains. The stereoselectivity of glycosylations is exceedingly difficult to control due to the reaction's high degree of sensitivity and its shifting, simultaneous mechanistic pathways that are controlled by variables of unknown degree of influence, dominance, or interdependency. An automated platform was devised to quickly, reproducibly, and systematically screen glycosylations and thereby address this fundamental problem. Thirteen variables were investigated in as isolated a manner as possible, to identify and quantify inherent preferences of electrophilic glycosylating agents (glycosyl donors) and nucleophiles (glycosyl acceptors). Ways to enhance, suppress, or even override these preferences using judicious environmental conditions were discovered. Glycosylations involving two specific partners can be tuned to produce either 11:1 selectivity of one stereoisomer or 9:1 of the other by merely changing the reaction conditions.