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 
• 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

• 28140-37-6 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 121238-27-5 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate 
• 38430-69-2 Benzoic acid (3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 109922-74-9 Benzoic acid (2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 109922-75-0 Benzoic acid (2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester 
• 139710-25-1 (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 141607-25-2 (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 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 
• 942428-90-2 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 886442-17-7 (3'-benzyloxycarbonylpropyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 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 

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.

Nanoparticles to Study Lectins in Caenorhabditis elegans: Multivalent Galactose β1-4 Fucose-Functionalized Dendrimers Provide Protection from Oxidative Stress

Galectins are galactoside-binding lectins that are functional dimers or higher-order oligomers. Multivalent binding has been shown to augment the relatively low affinity of the galectins for their galactoside-binding partners, enabling the galectins to pl

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.

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.

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.

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.