83-87-4

Basic information

• Product Name: BETA-D-GLUCOSE PENTAACETATE
• Synonyms: 1,2,3,4,6-PENTA-O-ACETYL-B-D-GLUCOPYRANOSE;1,2,3,4,6-PENTAACETYL-ALPHA-D-GLUCOSE;1,2,3,4,6-PENTA-O-ACETYL-BETA-D-GLUCOSE;B-D-GLUCOSE PENTAACETATE;B-D-1,2,3,4,6-PENTA-O-ACETYL-B-GLUCOPYRANOSE;BETA-D-GLUCOPYRANOSE-PENTAACETATE;BETA-DEXTROSE PENTAACETATE;D-B-GLUCOSE PENTAACETATE
• CAS NO: 83-87-4
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• EINECS: 210-074-8
• Product Categories: API intermediates
• Mol File: 83-87-4.mol
• Article Data: 301

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 452 °C
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• Storage Temp.: 0-6°C
• Solubility: chloroform: 0.1 g/mL, clear, colorless
• Water Solubility: chloroform: 0.1 g/mL, clear, colorless
• CAS DataBase Reference: BETA-D-GLUCOSE PENTAACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-D-GLUCOSE PENTAACETATE(83-87-4)
• EPA Substance Registry System: BETA-D-GLUCOSE PENTAACETATE(83-87-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 83-87-4(Hazardous Substances Data)

Usage

Description

BETA-D-GLUCOSE PENTAACETATE is a chemical compound derived from glucose through the process of acetylation. It is odorless with a bitter flavor and can be synthesized using various techniques such as ZnCl2 and pyridine, sodium acetate, and acetic anhydride and pyridine.

Uses

Used in Pharmaceutical Industry:
BETA-D-GLUCOSE PENTAACETATE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable building block for the development of new drugs.
Used in Chemical Synthesis:
BETA-D-GLUCOSE PENTAACETATE is used as a reagent in various chemical synthesis processes. Its ability to undergo various chemical reactions makes it a versatile compound for creating a wide range of products.
Used in Research and Development:
BETA-D-GLUCOSE PENTAACETATE is used in research and development for studying the properties and behavior of glucose and its derivatives. It can provide valuable insights into the structure, function, and potential applications of glucose-based compounds.

Upstream product

• 7322-31-8 β-D-mannose 
• 108-24-7 acetic anhydride 
• 530-26-7 D-Mannose 
• 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 
• 75-36-5 acetyl chloride 
• 3458-28-4 D-Mannose 
• 2280-44-6 D-Glucose 
• 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 

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

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.

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation

Glycodendrimers are receiving considerable attention to mimic a number of imperative features of cell surface glycoconjugate and acquired excellent relevance to a wide domain of investigations including medicine, pharmaceutics, catalysis, nanotechnology, carbohydrate-protein interaction, and moreover in drug delivery systems. Toward this end, an expeditious, modular, and regioselective triazole-forming CuAAC click approach along with double stage convergent synthetic method was chosen to develop a variety of novel chlorine-containing cyclen cored glycodendrimers of high sugar tethers at low generation of promising therapeutic potential. We developed a novel chlorine-containing hypercore unit with 12 alkynyl functionality originated from cyclen scaffold which was confirmed by its single crystal X-ray data analysis. Further, the modular CuAAC technique was utilized to produce a variety of novel 12–sugar coated (G0) glycodendrimers 12-15 adorn with β-Glc-, β-Man-, β-Gal-, β-Lac, along with 36-galactose coated (G1) glycodendrimer 18 in good-to-high yield. The structures of the developed glycodendrimer architectures have been well elucidated by extensive spectral analysis including NMR (1H & 13CNMR), HRMS, MALDI-TOF MS, UV–Vis, IR, and SEC (Size Exclusion Chromatogram) data.