5019-25-0

Basic information

• Product Name: Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside
• Synonyms: Methyl 2-O,3-O,4-O,6-O-tetraacetyl-β-D-mannopyranoside;NSC 1963
• CAS NO: 5019-25-0
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 0
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 5019-25-0.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 407.3°Cat760mmHg
• Flash Point: 176.1°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 7.62E-07mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside(5019-25-0)
• EPA Substance Registry System: Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside(5019-25-0)

Safety Data

• Hazardous Substances Data: 5019-25-0(Hazardous Substances Data)

Usage

Description

Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside, with the CAS number 5019-25-0, is a derivative of b-D-mannopyranoside, a monosaccharide commonly found in nature. Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside is characterized by the presence of four acetyl groups attached to the 2, 3, 4, and 6 positions of the sugar molecule. It is a versatile intermediate in organic synthesis, particularly in the preparation of various complex carbohydrates and glycoconjugates.

Uses

Used in Organic Synthesis:
Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside is used as a synthetic intermediate for the preparation of various complex carbohydrates and glycoconjugates. Its application in organic synthesis is due to its ability to serve as a building block for the construction of more intricate carbohydrate structures, which are essential components of many biologically active molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside is used as a key component in the synthesis of glycoconjugate drugs. These drugs often have enhanced solubility, stability, and bioavailability compared to their non-glycosylated counterparts. Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside's role in the pharmaceutical industry is to facilitate the development of novel therapeutic agents with improved pharmacological properties.
Used in Research and Development:
Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside is also utilized in research and development for the study of carbohydrate chemistry and glycobiology. It serves as a valuable tool for understanding the structure, function, and interactions of carbohydrates in biological systems. Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside's use in research and development is crucial for advancing our knowledge of carbohydrate-based therapeutics and their potential applications in medicine.
Used in Material Science:
In the field of material science, Methyl 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranoside can be employed in the development of carbohydrate-based materials with unique properties. These materials may find applications in areas such as drug delivery, tissue engineering, and biosensors, where the incorporation of carbohydrates can provide specific recognition, targeting, or biocompatibility properties.

InChI:InChI=1/C15H22O10/c1-7(16)21-6-11-12(22-8(2)17)13(23-9(3)18)14(24-10(4)19)15(20-5)25-11/h11-15H,6H2,1-5H3/t11-,12+,13+,14-,15-/m1/s1

Upstream product

• 67-56-1 methanol 
• 13242-53-0 acetobromomannose 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 182064-04-6 (2R,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 3458-28-4 D-Mannose 
• 108-24-7 acetic anhydride 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 51224-39-6 methyl β-D-glucopyranoside 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 97-30-3 methyl D-glucopyranoside 
• 66118-22-7 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-isocyanotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 79378-78-2 2,3,4,6-Tetra-O-acetyl-1-O-(p-tolylsulfinyl)-α-D-glucopyranose 

Downstream Products

• 93768-42-4 methyl-(tetra-O-benzoyl-β-D-mannopyranoside) 
• 604-70-6 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 269056-16-8 1,2,3,4,5,6-hexa-O-acetyl-D-mannose methyl hemiacetal 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 91602-61-8 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 2936-70-1 phenyl 1-thio-D-glucopyranoside 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-mannopyranoside 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 

Relevant articles and documents

General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2- trans-Diols to 1,2- cis-Diols

Human glycans are primarily composed of nine common sugar building blocks. On the other hand, several hundred monosaccharides have been discovered in bacteria and most of them are not readily available. The ability to access these rare sugars and the corresponding glycoconjugates can facilitate the studies of various fundamentally important biological processes in bacteria, including interactions between microbiota and the human host. Many rare sugars also exist in a variety of natural products and pharmaceutical reagents with significant biological activities. Although several methods have been developed for the synthesis of rare monosaccharides, most of them involve lengthy steps. Herein, we report an efficient and general strategy that can provide access to rare sugars from commercially available common monosaccharides via a one-step Ru(II)-catalyzed and boron-mediated selective epimerization of 1,2-trans-diols to 1,2-cis-diols. The formation of boronate esters drives the equilibrium toward 1,2-cis-diol products, which can be immediately used for further selective functionalization and glycosylation. The utility of this strategy was demonstrated by the efficient construction of glycoside skeletons in natural products or bioactive compounds.

Structural properties of D-mannopyranosyl rings containing O-Acetyl side-chains

The crystal structures of 1,2,3,4,6-penta-O-Acetyl--d-mannopyranose, C16H22O11, and 2,3,4,6-Tetra-O-Acetyl--d-mannopyranosyl-(1.2)-3,4,6-Tri-O-Acetyl--d-mannopyranosyl-( 1.3)-1,2,4,6-Tetra-O-Acetyl--d-mannopyranose, C40H54O27, were determined and compared to those of methyl 2,3,4,6-Tetra-O-Acetyl--d-mannopyranoside, methyl -d-mannopyranoside andmethyl -d-mannopyranosyl-(1.2)--d-mannopyranoside to evaluate the effects of O-Acetylation on bond lengths, bond angles and torsion angles. In general, O-Acetylation exerts little effect on the exo-and endocyclic C-C and endocyclic C-O bond lengths, but the exocyclic C-O bonds involved in O-Acetylation are lengthened by -0.02 A ° . The conformation of the O-Acetyl side-chains is highly conserved, with the carbonyl O atom either eclipsing the H atom attached to a 2-Alcoholic C atom or bisecting the H-C-H bond angle of a 1-Alcoholic C atom. Of the two C-O bonds that determine O-Acetyl side-chain conformation, that involving the alcoholic C atom exhibits greater rotational variability than that involving the carbonyl C atom. These findings are in good agreement with recent solution NMR studies of O-Acetyl side-chain conformations in saccharides. Experimental evidence was also obtained to confirm density functional theory (DFT) predictions of C-O and O-H bond-length behavior in a C-O-H fragment involved in hydrogen bonding.

One-pot oxidation-hydrocyanation sequence coupled to lipase-catalyzed diastereoresolution in the chemoenzymatic synthesis of sugar cyanohydrin esters

A three-step, one-pot synthesis and diastereoresolution sequence is described in anhydrous toluene starting from methyl α-D-2,3,4-tri-O- acetylgalacto- (1a), -manno- (1b) and -glucopyranosides (1c). The reaction sequence, including consecutive transformations through the aldehyde [PhI(OAc)2, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)] and cyanohydrin [basic resin or (R)-oxynitrilase] into the (6R)-cyanohydrin ester (lipase) is shown to proceed in a one-pot cascade, except that the basic resin (when used) should be removed before the addition of the enzymatic acylation reagents. We have shown that the effective transformation of 1a (75 % reaction yield) through labile intermediates gives the stable (6R)-cyanohydrin butanoate (85 % de). Further diastereomeric purification by chromatography is possible, although the product is already of high diastereopurity. (6R)-Cyanohydrin esters are obtained through acylation with Burkholderia cepacia lipase. The (6S)-ester (de 99 %) is produced by Candida rugosa lipase when the sequence is started from 1c whereas the other sugar derivatives are less suited to the reaction with lipase. Copyright