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 
• 5019-25-0 methyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 56-75-7 chloramphenicol 
• 4163-60-4 β-D-galactose peracetate 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 64-19-7 acetic acid 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 492-62-6 alpha-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 75-36-5 acetyl chloride 
• 127-08-2 potassium acetate 

Downstream Products

• 16977-78-9 2'-bromoethyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 16977-78-9 2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 174196-05-5 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-4,6-diphenyl-2-thioxo-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 174196-09-9 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-4-phenyl-2-thioxo-6-p-tolyl-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 174196-07-7 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-cyano-4-phenyl-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 174196-19-1 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-4-furan-2-yl-2-thioxo-6-p-tolyl-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 174196-11-3 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-cyano-4-(4-methoxy-phenyl)-6-phenyl-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 174196-21-5 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 174196-15-7 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-cyano-4-(4-methoxy-phenyl)-2-thioxo-6-p-tolyl-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 174196-17-9 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-cyano-4-furan-2-yl-6-phenyl-2-thioxo-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 174196-13-5 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-cyano-4-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 128299-95-6 n-octyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 

Relevant articles and documents

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

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.

A Sweet H2S/H2O2Dual Release System and Specific Protein S-Persulfidation Mediated by Thioglucose/Glucose Oxidase

H2S and H2O2 are two redox regulating molecules that play important roles in many physiological and pathological processes. While each of them has distinct biosynthetic pathways and signaling mechanisms, the crosstalk between these two species is also known to cause critical biological responses such as protein S-persulfidation. So far, many chemical tools for the studies of H2S and H2O2 have been developed, such as the donors and sensors for H2S and H2O2. However, these tools are normally targeting single species (e.g., only H2S or only H2O2). As such, the crosstalk and synergetic effects between H2S and H2O2 have hardly been studied with those tools. In this work, we report a unique H2S/H2O2 dual donor system by employing 1-thio-β-d-glucose and glucose oxidase (GOx) as the substrates. This enzymatic system can simultaneously produce H2S and H2O2 in a slow and controllable fashion, without generating any bio-unfriendly byproducts. This system was demonstrated to cause efficient S-persulfidation on proteins. In addition, we expanded the system to thiolactose and thioglucose-disulfide; therefore, additional factors (β-galactosidase and cellular reductants) could be introduced to further control the release of H2S/H2O2. This dual release system should be useful for future research on H2S and H2O2.