6207-76-7

Usage

Uses

Used in Carbohydrate Chemistry Research:
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranose is used as a protecting group for hydroxyl groups in carbohydrate chemistry, allowing for selective reactions and manipulation of other functional groups in the molecule. Its ability to be easily removed under mild conditions makes it a valuable tool in the synthesis of complex carbohydrates and glycoconjugates.
Used in Organic Chemistry:
In the field of organic chemistry, 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranose is utilized as a key building block for the synthesis of various organic compounds. Its protective properties and ease of removal contribute to its significance in the development of novel organic molecules and structures.
Used in Pharmaceutical Industry:
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranose is employed as a starting material or intermediate in the synthesis of pharmaceutical compounds, particularly those involving carbohydrate-based structures. Its protective properties facilitate the synthesis of complex carbohydrate-based drugs and enhance the efficiency of the drug development process.
Used in Biochemical Research:
In biochemical research, 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranose is used as a model compound to study the interactions of carbohydrates with proteins, enzymes, and other biomolecules. Its protective groups allow for controlled experiments and provide insights into the role of carbohydrates in biological systems.
Used in Material Science:
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranose is utilized in the development of carbohydrate-based materials, such as hydrogels, films, and coatings. Its protective properties and ease of removal contribute to the fabrication of materials with tailored properties and functions, including stimuli-responsive materials and biocompatible coatings.

Upstream product

• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 13242-53-0 acetobromomannose 
• 83-87-4 D-Mannose pentaacetate 
• 530-26-7 D-Mannose 
• 108-24-7 acetic anhydride 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 108-95-2 phenol 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 165053-18-9 3,4,6-tri-O-acetyl-1,2-O-vinylidene-β-D-mannopyranose 
• 17042-40-9 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-1-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 
• 4851-64-3 phosphoric acid diethyl ester vinyl ester 

Downstream Products

• 439-03-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl fluoride 
• 637004-85-4 (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 252209-20-4 phenyl 4,6-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 252209-21-5 phenyl 3-O-benzyl-4,6-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 252209-22-6 phenyl 2-O-acetyl-3-O-benzyl-4,6-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 849063-71-4 benzyl {{[(S)-2-hydroxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate 
• 637004-86-5 benzyl {{[(S)-2-allyloxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate 
• 85249-43-0 allyl-β-D-mannopyranoside 
• 316382-36-2 allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-4-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 
• 316382-37-3 allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 
• 251547-30-5 C₄₃H₇₅BrO₁₄ 
• 251547-32-7 Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(12-{3-bromomethyl-5-[12-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-dodecyloxy]-phenoxy}-dodecyloxy)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy

Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.

An alternative approach for the synthesis of sulfoquinovosyldiacylglycerol

Sulfoquinovosyldiacylglycerol (SQDG) is a glycolipid ubiquitously found in photosyn-thetically active organisms. It has attracted much attention in recent years due to its biological ac-tivities. Similarly, the increasing demand for vegan and functional foods has led to a growing interest in micronutrients such as sulfolipids and their physiological influence on human health. To study this influence, reference materials are needed for developing new analytical methods and providing enough material for model studies on the biological activity. However, the availability of these materials is limited by the difficulty to isolate and purify sulfolipids from natural sources and the unavailability of chemical standards on the market. Consequently, an alternative synthetic route for the comprehensive preparation of sulfolipids was established. Here, the synthesis of a sulfolipid with two identical saturated fatty acids is described exemplarily. The method opens possibilities for the preparation of a diverse range of interesting derivatives with different saturated and unsatu-rated fatty acids.

Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides

N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.

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.

Rh2(II)-Catalyzed intermolecular N-Aryl aziridination of olefins using nonactivated N atom precursors

The development of the first intermolecular Rh2(II)-catalyzed aziridination of olefins using anilines as nonactivated N atom precursors and an iodine(III) reagent as the stoichiometric oxidant is reported. This reaction requires the transfer of an N-aryl nitrene fragment from the iminoiodinane intermediate to a Rh2(II) carboxylate catalyst; in the absence of a catalyst only diaryldiazene formation was observed. This N-aryl aziridination is general and can be successfully realized by using as little as 1 equiv of the olefin. Di-, tri-, and tetrasubstituted cyclic or acylic olefins can be employed as substrates, and a range of aniline and heteroarylamine N atom precursors are tolerated. The Rh2(II)-catalyzed N atom transfer to the olefin is stereospecific as well as chemo- and diastereoselective to produce the N-aryl aziridine as the only amination product. Because the chemistry of nonactivated N-aryl aziridines is underexplored, the reactivity of N-aryl aziridines was explored toward a range of nucleophiles to stereoselectively access privileged 1,2-stereodiads unavailable from epoxides, and removal of the N-2,4-dinitrophenyl group was demonstrated to show that functionalized primary amines can be constructed.

Total synthesis of three natural phenethyl glycosides

Phenethyl glycosides having phenolic or methoxy functions at benzene rings are substances widely occurring in nature. This kind of compounds has been shown to have anti-oxidant, anti-inflammatory, and anticancer activities. However, some of them are not naturally abundant, thus the synthesis of such molecules is desirable. In this paper, natural phenethyl glycosides 3 and 4 were first totally synthesized from easily available materials with overall yields of 50.5% and 40.1%, respectively. And a new synthetic route to obtain natural phenethyl glycoside 2 in 46.2% yield was also described.

First total syntheses of two natural glycosides

Isosyringinoside (1) and 3-(O-β-D-glucopyranosyl)-α-(O-β-D-glucopyranosyl)-4-hydroxy phenylethanol (2), the natural bioactive compounds contained unique structures, were first totally synthesized using easily available materials in short convenient routes with overall yields of 20.2% and 27.0%, respectively. An efficient total synthesis of 1 was developed in six steps, which contained two key steps of highly regioselective glycosylation without any selective protection steps. The seven-step synthesis of 2 involved two steps of regioselective glycosylations using BF3–O(C2H5)2 and TMSOTf as catalysts, respectively.

Scalable Total Synthesis of Piceatannol-3′-O-β-d-glucopyranoside and the 4′-Methoxy Congener Thereof: An Early Stage Glycosylation Strategy

Scalable syntheses of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative, and a key Mizoroki.Heck reaction to render the desired coupled products in high overall yield.

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

A gulose moiety contributes to the belomycin (BLM) disaccharide selective targeting to lung cancer cells

Eight mono- or disaccharide analogues derived from BLM disaccharide, along with the corresponding carbohydate-dye conjugates have been designed and synthesized in this study, aiming at exploring the effect of a gulose residue on the cellular binding/uptake of BLM disaccharide and it possible uptake mechanism. Our evidence is presented indicating that, for the cellular binding/uptake of BLM disaccharide, a gulose residue is an essential subunit but unrelated to its chemical nature. Interestingly, D-gulose-dye conjugate is able to selectively target A549 cancer cells, but L-gulose-dye conjugate fails. Further uptake mechanism studies demonstrate D-gulose-dye derivatives similar to BLM disaccharide-dye ones behave in a temperature- and ATP-dependent manner, and are partly directed by the GLUT1 receptor. Moreover, D-gulose modifying gemcitabine 53a exhibits more potent antitumor activity compared to derivatives 53b-c in which gemcitabine is decorated with other monosaccharides. Taken together, the monosacharide D-gulose conjugate offers a new strategy for solving cytotoxic drugs via the increased tumor targeting in the therapy of lung cancer.