140147-37-1

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-D-mannopyranose
• Synonyms: 2,3,4,6-Tetra-O-acetyl-D-mannopyranose;D-Mannopyranose tetraacetate;(2R,3R,4S,5S)-2-(AcetoxyMethyl)-6-hydroxytetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 140147-37-1
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.3
• Mol File: 140147-37-1.mol

Chemical Properties

• Melting Point: 92-95°C
• Boiling Point: 418.399 °C at 760 mmHg
• Flash Point: 145.58 °C
• Appearance: /
• Density: 1.339 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate, Methanol
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-D-mannopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-D-mannopyranose(140147-37-1)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-D-mannopyranose(140147-37-1)

Safety Data

• Hazardous Substances Data: 140147-37-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3,4,6-Tetra-O-acetyl-D-mannopyranose is used as a building block in organic synthesis for the creation of other complex molecules. Its acetylated hydroxyl groups provide versatility in chemical reactions, allowing for the formation of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,6-Tetra-O-acetyl-D-mannopyranose is used as a starting material for the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a promising candidate for the development of new drugs with potential therapeutic applications.
Used in Carbohydrate Chemistry:
2,3,4,6-Tetra-O-acetyl-D-mannopyranose is utilized in the field of carbohydrate chemistry due to its potential applications in the creation of complex carbohydrate structures. Its acetylated hydroxyl groups facilitate the formation of glycosidic linkages, which are essential for the synthesis of oligosaccharides and polysaccharides.
Used in Synthesis of Glycosides:
2,3,4,6-Tetra-O-acetyl-D-mannopyranose is used as a starting material for the synthesis of various glycosides, which are important molecules in biological systems. Glycosides play crucial roles in numerous biological processes, including cell recognition, signal transduction, and drug metabolism. The synthesis of these molecules using 2,3,4,6-Tetra-O-acetyl-D-mannopyranose can contribute to the development of new therapeutic agents and diagnostic tools.

Upstream product

• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 13242-53-0 acetobromomannose 
• 26302-39-6 N-p-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 74352-37-7 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(pyridin-2-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 199481-19-1 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,3R)-3-acetyl-3-methyl-oxiranyloxy)-tetrahydro-pyran-3-yl ester 
• 76-05-1 trifluoroacetic acid 
• 174647-49-5 2-nonyn-1-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 35785-63-8 2,3,4,6-tetra-O-acetyl-1-deoxy-1-(p-nitrobenzylthio)-β-D-glucopyranose 
• 142266-54-4 1,3-thiazolin-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 762-04-9 phosphonic acid diethyl ester 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 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 
• 251547-34-9 Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(12-{3-hydroxymethyl-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 
• 1314918-20-1 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl ortho-hexynylbenzoate 
• 1314918-19-8 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl ortho-hexynylbenzoate 
• 6605-40-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 439-01-0 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl fluoride 
• 1352278-39-7 (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 1352427-79-2 (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,3,4,6-tetra-O-benzoyl-β-D-mannopyranoside 
• 132153-84-5 2-O-(α-D-mannosyl)hydroxyethyl methacrylate 
• 17042-40-9 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-1-α-D-mannopyranoside 
• 29073-91-4 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 604767-74-0 di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl) phosphate 

Relevant articles and documents

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.

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.

Mannose-modified azide exosome and application thereof

The invention belongs to the field of biological medicine, and particularly relates to a mannose-modified azide exosome and an application thereof. The mannose-modified azide exosome is prepared through metabolic labeling and click chemistry reaction; the advantages of the surface-functionalized azide exosome targeting macrophages are determined through a flow cytometry on the cellular level, and in-vitro pharmacological experiments prove that the mannose-modified azide exosome has the advantage of treating infectious diseases after being loaded with drugs. According to the surface-functionalized azide exosome provided by the invention, the targeting property of the exosome as a drug carrier can be greatly improved, and the effect of the surface-functionalized azide exosome in treating refractory infectious related diseases is improved.

Preparation and formulation optimization of methotrexate-loaded human serum albumin nanoparticles modified by mannose

Background: Methotrexate (MTX) is the representative drug among the dis-ease-modifying anti-rheumatic drugs. However, the conventional treatment with MTX showed many limitations and side effects. Objective: To strengthen the targeting ability and circulation time of MTX in the treatment of rheumatoid arthritis, the present study focused on developing a novel drug delivery system of methotrexate-loaded human serum albumin nanoparticles (MTX-NPs) modified by mannose, which are referred to as MTX-M-NPs. Methods: Firstly, mannose-derived carboxylic acid was synthesized and further modified on the surface of MTX-NPs to prepare MTX-M-NPs. The formulation of nanoparticles was optimized by the method of central composite design (CCD), with the drug lipid ra-tio, oil-aqueous ratio, and cholesterol or lecithin weight as the independent variables. The average particle size and encapsulation efficiency were the response variables. The response of different formulations was calculated, and the response surface diagram, con-tour diagram, and mathematical equation were used to relate the dependent and independent variables to predict the optimal formula ratio. The uptake of MTX-M-NPs by neu-trophils was studied through confocal laser detection. Further, MTX-M-NPs were subject-ed to assessment of the pharmacokinetics profile after intravenous injection with Sprague-Dawley rats. Results: This targeting drug delivery system was successfully developed. Results from Nuclear Magnetic Resonance and Fourier Transform Infrared Spectroscopy analysis can verify the successful preparation of this drug delivery system. Based on the optimized for-mula, MTX-M-NPs were prepared with a particle size of 188.17 ± 1.71 nm and an encapsulation rate of 95.55 ± 0.33%. MTX-M-NPs displayed significantly higher cellular uptake than MTX-NPs. The pharmacokinetic results showed that MTX-M-NPs could pro-long the in vivo circulation time of MTX. Conclusion: This targeting drug delivery system laid a promising foundation for the treatment of RA.

Fluorinated rhamnosides inhibit cellular fucosylation

The sugar fucose is expressed on mammalian cell membranes as part of glycoconjugates and mediates essential physiological processes. The aberrant expression of fucosylated glycans has been linked to pathologies such as cancer, inflammation, infection, and genetic disorders. Tools to modulate fucose expression on living cells are needed to elucidate the biological role of fucose sugars and the development of potential therapeutics. Herein, we report a class of fucosylation inhibitors directly targeting de novo GDP-fucose biosynthesis via competitive GMDS inhibition. We demonstrate that cell permeable fluorinated rhamnose 1-phosphate derivatives (Fucotrim I & II) are metabolic prodrugs that are metabolized to their respective GDP-mannose derivatives and efficiently inhibit cellular fucosylation.

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.