55286-97-0

Basic information

• Product Name: 1,2,3,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE
• Synonyms: 1,2,3,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE;1,2,3,6-Tetra-O-acetyl-a-D-glucopyranose
• CAS NO: 55286-97-0
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.3
• Mol File: 55286-97-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 433.823 °C at 760 mmHg
• Flash Point: 152.355 °C
• Appearance: /
• Density: 1.339 g/cm³
• PKA: 12.47±0.70(Predicted)
• CAS DataBase Reference: 1,2,3,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE(55286-97-0)
• EPA Substance Registry System: 1,2,3,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE(55286-97-0)

Safety Data

• Hazardous Substances Data: 55286-97-0(Hazardous Substances Data)

Usage

General Description

1,2,3,6-Tetra-O-acetyl-alpha-D-glucopyranose is a chemical compound that is derived from glucose. It is a white crystalline solid with a molecular formula of C14H20O10 and a molecular weight of 348.3 g/mol. 1,2,3,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE is commonly used in organic synthesis and as a protecting group in carbohydrate chemistry. It is also used as a precursor in the synthesis of other organic compounds and as a building block in the production of pharmaceuticals. 1,2,3,6-Tetra-O-acetyl-alpha-D-glucopyranose is stable under normal temperatures and pressures, and it is soluble in certain organic solvents. It is important to handle this compound with care and follow appropriate safety precautions due to its potential hazards and toxicity.

Upstream product

• 71208-20-3 1,2,3,4-tetra-O-acetyl-6-O-benzoyl-α-D-glucopyranose 
• 83-87-4 D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 10028-44-1 1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucopyranose 

Downstream Products

• 79414-65-6 1,2,3,6-tetra-O-acetyl-4-O-benzyl-α-D-glucopyranose 
• 108257-54-1 1,2,3,6-tetra-O-acetyl-4-O-trityl-α-D-glucopyranose 

Relevant articles and documents

Novel and efficient chemoenzymatic synthesis of D-glucose 6-phosphate and molecular modeling studies on the selective biocatalysis

A concise chemoenzymatic synthesis of glucose 6-phosphate is described. Candida rugosa lipase was found to be an efficient catalyst for both regio- and stereoselective deacetylation of the primary hydroxy group in the peracetylated D-glucose. In addition, we report an improved synthesis of 1,2,3,4,6-penta-O- acetyl-α-D-glucopyranose providing a large-scale procedure for the acetylation of α-D-glucose without isomerization at the anomeric center. The high overall yield and the easy scalability makes this chemoenzymatic strategy attractive for industrial application. Furthermore, molecular modeling of phosphonate transition-state analog for the enzymatic hydrolysis step supports the substrate selectivity observed with Candida rugosa lipase. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Regioselective hydrolysis of peracetylated α-D-glucopyranose catalyzed by immobilized lipases in aqueous medium. A facile preparation of useful intermediates for oligosaccharide synthesis

Penta-O-acetyl-α-D-Glucopyranose was selectively deacetylated in aqueous media by lipases from Candida cilindracea (CCL) adsorbed on octyl- agarose support. Enzymatic hydrolyses was regioselective at the 4-position under neutral pH and towards the 6 position under acidic conditions. This enzymatic approach allows the one step synthesis of 1,2,3,6-tetra-O-acetyl- α-D-glucopyranoses 1, a useful intermediate in oligosaccharide synthesis.