2152-77-4

Usage

Uses

Used in Pharmaceutical Industry:
Pentaacetate α-L-Idopyranose is used as a synthetic building block for the creation of mucopolysaccharides, which are essential components of various biological systems. These mucopolysaccharides can act as antagonist agents, potentially playing a role in the development of new therapeutic strategies for various diseases.
Used in Chemical Synthesis:
As a white solid with unique chemical properties, Pentaacetate α-L-Idopyranose can be utilized in various chemical synthesis processes. Its acetate groups can be manipulated to produce a range of compounds with different applications in the chemical, pharmaceutical, and materials science industries.

Upstream product

• 7322-31-8 β-D-mannose 
• 108-24-7 acetic anhydride 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 5019-25-0 methyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 10257-28-0 D-Galactose 
• 56-75-7 chloramphenicol 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 64-19-7 acetic acid 
• 17460-45-6 tetra-acetyl glucosamine 
• 75-36-5 acetyl chloride 
• 7296-15-3 alpha-D-mannopyranoside 
• 552-76-1 D-mannose 

Downstream Products

• 13242-51-8 1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside 
• 125354-48-5 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 37797-55-0 1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 14227-52-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 13242-53-0 acetobromomannose 
• 6087-47-4 O³,O⁴,O⁶-triacetyl-O²-trichloroacetyl-β-D-mannopyranosyl chloride 
• 74590-42-4 o-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 28619-26-3 p-cresyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 134698-99-0 phenylethyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 134698-98-9 p-phenylphenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Selectivity of 1-O-Propargyl-D-Mannose Preparations

Thanks to their ability to bind to specific biological receptors, mannosylated structures are examined in biomedical applications. One of the most common ways of linking a functional moiety to a structure is to use an azide-alkyne click reaction. Therefore, it is necessary to prepare and isolate a propargylated mannose derivative of high purity to maintain its bioactivity. Three known preparations of propargyl-α-mannopyranoside were revisited, and products were analysed by NMR spectroscopy. The preparations were shown to yield by-products that have not been described in the literature yet. Our experiments showed that one-step procedures could not provide pure propargyl-α-mannopyranoside, while a three-step procedure yielded the desired compound of high purity.

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity

Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

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.

Protecting carbohydrates with ethers, acetals and orthoesters under basic conditions

Chlorinated ethyl and vinyl ethers are introduced at various positions of carbohydrates. Depending on the relative stereochemistry, vinylethers, acetals or orthoesters are formed under basic conditions. The products are stable, but are easily deprotected

CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation

Glycodendrimers are receiving considerable attention to mimic a number of imperative features of cell surface glycoconjugate and acquired excellent relevance to a wide domain of investigations including medicine, pharmaceutics, catalysis, nanotechnology, carbohydrate-protein interaction, and moreover in drug delivery systems. Toward this end, an expeditious, modular, and regioselective triazole-forming CuAAC click approach along with double stage convergent synthetic method was chosen to develop a variety of novel chlorine-containing cyclen cored glycodendrimers of high sugar tethers at low generation of promising therapeutic potential. We developed a novel chlorine-containing hypercore unit with 12 alkynyl functionality originated from cyclen scaffold which was confirmed by its single crystal X-ray data analysis. Further, the modular CuAAC technique was utilized to produce a variety of novel 12–sugar coated (G0) glycodendrimers 12-15 adorn with β-Glc-, β-Man-, β-Gal-, β-Lac, along with 36-galactose coated (G1) glycodendrimer 18 in good-to-high yield. The structures of the developed glycodendrimer architectures have been well elucidated by extensive spectral analysis including NMR (1H & 13CNMR), HRMS, MALDI-TOF MS, UV–Vis, IR, and SEC (Size Exclusion Chromatogram) data.

First total syntheses of four natural bioactive glucosides

The efficient total syntheses of four biologically interesting natural glucosides Ethylconiferin, Butylconiferin, 2’-Butoxyethylconiferin and Balajaponin B, have been achieved for the first time starting from commercially available Vanilline via concise reaction sequence of 8–10 steps with the overall yield of 26–41%. This work definitely laid the foundation for the further pharmacological study of this kind of natural compounds. Meanwhile, currently developed approach could be used as a general synthetic strategy for the syntheses of other monolignol glucosides and their derivatives, and provides an opportunity for further study of the structure-activity relationship of this kind of glucosides.

Inhibition of S. aureus Infection of Human Umbilical Vein Endothelial Cells (HUVECs) by Trehalose- and Glucose-Functionalized Gold Nanoparticles

Microbial adhesion to host cells represents the initial step in the infection process. Several methods have been explored to inhibit microbial adhesion including the use of glycopolymers based on mannose, galactose, sialic acid and glucose. These sugar re

A Sweet H2S/H2O2Dual Release System and Specific Protein S-Persulfidation Mediated by Thioglucose/Glucose Oxidase

H2S and H2O2 are two redox regulating molecules that play important roles in many physiological and pathological processes. While each of them has distinct biosynthetic pathways and signaling mechanisms, the crosstalk between these two species is also known to cause critical biological responses such as protein S-persulfidation. So far, many chemical tools for the studies of H2S and H2O2 have been developed, such as the donors and sensors for H2S and H2O2. However, these tools are normally targeting single species (e.g., only H2S or only H2O2). As such, the crosstalk and synergetic effects between H2S and H2O2 have hardly been studied with those tools. In this work, we report a unique H2S/H2O2 dual donor system by employing 1-thio-β-d-glucose and glucose oxidase (GOx) as the substrates. This enzymatic system can simultaneously produce H2S and H2O2 in a slow and controllable fashion, without generating any bio-unfriendly byproducts. This system was demonstrated to cause efficient S-persulfidation on proteins. In addition, we expanded the system to thiolactose and thioglucose-disulfide; therefore, additional factors (β-galactosidase and cellular reductants) could be introduced to further control the release of H2S/H2O2. This dual release system should be useful for future research on H2S and H2O2.