4163-59-1

Basic information

• Product Name: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE
• Synonyms: 1,2,3,4,6-Penta-O-acetyl-α-D-galactopyranose ,98%;1,2,3,4,6-Penta-O-acetyl-alpha-D-galactose;2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl acetate;alpha-D-Galactopyranose 1,2,3,4,6-pentaacetate;alpha-D-Galactopyranose pentaacetate;Penta-O-acetyl-a-D-galactopyranoside;ALPHA-D-GALACTOSE-PENTAACETATE;1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE
• CAS NO: 4163-59-1
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• EINECS: 1312995-182-4
• Mol File: 4163-59-1.mol
• Article Data: 301

Chemical Properties

• Melting Point: 95-96℃
• Boiling Point: 435℃
• Flash Point: 188℃
• Appearance: White to Off-white/Powder
• Density: 1.30
• Vapor Pressure: 9.23E-08mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in methanol at approximately 50mg/ml
• CAS DataBase Reference: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(4163-59-1)
• EPA Substance Registry System: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(4163-59-1)

Safety Data

• Statements: 22
• Safety Statements: 36/37
• Hazardous Substances Data: 4163-59-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

1,2,3,4,6-pentaacetate-α-D-Galactopyranose has been used as a building block for oligosaccharides containing internal and terminal Galβ1-3GlcNAcβ fragments, and in acyl transfer reactions.

Definition

ChEBI: An O-acyl carbohydrate that consists of alpha-D-galactopyranose bearing five O-acetyl substituents.

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 
• 5019-25-0 methyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 130052-61-8 1,3,4,6-tetra-O-acetyl-2-O-trityl-α-D-galactopyranose 
• 135593-74-7 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate 
• 130052-60-7 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl thiocyanate 
• 10257-28-0 D-Galactose 
• 56-75-7 chloramphenicol 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 64-19-7 acetic acid 
• 17460-45-6 tetra-acetyl glucosamine 

Downstream Products

• 13242-51-8 1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl 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 
• 37797-55-0 1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 14227-52-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 13242-53-0 acetobromomannose 
• 6087-47-4 O³,O⁴,O⁶-triacetyl-O²-trichloroacetyl-β-D-mannopyranosyl chloride 
• 28140-37-6 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 140428-83-7 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 85618-26-4 n-octyl 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranoside 

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.

First total syntheses of four natural bioactive glucosides

The efficient total syntheses of four biologically interesting natural glucosides Ethylconiferin, Butylconiferin, 2’-Butoxyethylconiferin and Balajaponin B, have been achieved for the first time starting from commercially available Vanilline via concise reaction sequence of 8–10 steps with the overall yield of 26–41%. This work definitely laid the foundation for the further pharmacological study of this kind of natural compounds. Meanwhile, currently developed approach could be used as a general synthetic strategy for the syntheses of other monolignol glucosides and their derivatives, and provides an opportunity for further study of the structure-activity relationship of this kind of glucosides.