25941-03-1

Basic information

• Product Name: 1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE
• Synonyms: D-MANNOSE PENTAACETATE;1,2,3,4,6-PENTA-O-ACETYL-ALPHA/BETA-D-MANNOPYRANOSE;1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE;PENTA-O-ACETYL D-MANNOPYRANOSIDE;1,2,3,4,6-Pentaacetate D-Mannopyranose;D-Mannopyranose Pentaacetate;1,2,3,4,6-Penta-O-acetyl-D-mannopyranose ,98%;1,2,3,4,6-Pentaacetate
• CAS NO: 25941-03-1
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• Product Categories: Carbohydrates & Derivatives;Carbohydrates
• Mol File: 25941-03-1.mol
• Article Data: 301

Chemical Properties

• Melting Point: 68-70°C
• Boiling Point: 434.77 °C at 760 mmHg
• Flash Point: 188.052 °C
• Appearance: White to Off-white/Powder
• Density: 1.31 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: -20°C Freezer
• Solubility: Soluble in dichloromethane, ether, ethyl acetate, methanol, and
• CAS DataBase Reference: 1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE(25941-03-1)
• EPA Substance Registry System: 1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE(25941-03-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 25941-03-1(Hazardous Substances Data)

Usage

Description

1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE is a white to off-white solid that is a derivative of D-mannopyranose, a monosaccharide. It is characterized by the presence of five acetyl groups attached to its hydroxyl groups, which gives it unique chemical properties and makes it a versatile compound for various applications.

Uses

1. Used in Pharmaceutical Industry:
1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE is used as a key intermediate compound for the preparation of glycopyranoside phosphates. These glycopyranosides are essential for the treatment of T lymphocyte mediated inflammatory diseases, as they play a crucial role in modulating the immune response and reducing inflammation.
2. Used in Research and Development:
1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE is also used in the preparation of glycopyranoside phosphates for the study of T-lymphocyte mediated inflammatory diseases. 1,2,3,4,6-PENTA-O-ACETYL-D-MANNOPYRANOSE serves as an important tool for researchers to understand the underlying mechanisms of these diseases and develop novel therapeutic strategies.

InChI:InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12?,13-,14?,15-,16-/m1/s1

Upstream product

• 7322-31-8 β-D-mannose 
• 108-24-7 acetic anhydride 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 64-19-7 acetic acid 
• 17460-45-6 tetra-acetyl glucosamine 
• 2280-44-6 D-Glucose 
• 57-50-1 Sucrose 
• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 530-57-4 3,5-dimethoxy-4-hydroxybenzoic acid 
• 134-96-3 syringic aldehyde 
• 50-99-7 D-glucose 
• 75-36-5 acetyl chloride 

Downstream Products

• 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 
• 74590-40-2 p-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 28619-25-2 p-chlorophenyl α-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 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 58918-67-5 4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 1231607-43-4 methyl 4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzoate 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 

Relevant articles and documents

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.

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 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.