4132-28-9

Basic information

• Product Name: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
• Synonyms: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE;2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE, 98%, MIXTURE OF ANOMERS;3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol;2,3,4,6-TETRA-O-BENZYL-D -GLUCOPYRANOSE CRYSTALLINE;2,3,4,6-Tetra-O-benzyl-D-glucopyranose;2,3,4,6-TETRABENZYL-D-GLUCOSE;D-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylmethyl)-;2,3,4,6-TETRA-O-BENZYL-A-D-GLUCOPYRANOSIDE
• CAS NO: 4132-28-9
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.65
• EINECS: 1312995-182-4
• Product Categories: 13C & 2H Sugars;Biochemistry;Glucose;O-Substituted Sugars;Sugars;aldehydes;Carbohydrates & Derivatives;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;Carbohydrates;Carbohydrates A to;Carbohydrates P-ZBiochemicals and Reagents;Monosaccharide;Halogenated Heterocycles ,Pyrazoles
• Mol File: 4132-28-9.mol
• Article Data: 162

Chemical Properties

• Melting Point: 145-149 °C(lit.)
• Boiling Point: 672.378 °C at 760 mmHg
• Flash Point: 360.441 °C
• Appearance: White crystaline solid
• Density: 1.222 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: −20°C
• Solubility: Soluble in chloroform
• PKA: 11.87±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose(4132-28-9)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose(4132-28-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4132-28-9(Hazardous Substances Data)

Usage

Chemical Properties

White Crystaline Solid

Uses

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (cas# 4132-28-9) is a compound useful in organic synthesis.

InChI:InChI=1/C34H36O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-35H,21-25H2/t30-,31-,32+,33-,34?/m1/s1

Upstream product

• 127873-79-4 2-methoxyethyl α-D-glucopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 139903-49-4 phenyl 2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glycopyranoside 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 55722-48-0 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 89615-40-7 benzyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 78890-61-6 2-methoxyethyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 173597-19-8 p-methoxyphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 17042-40-9 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-1-α-D-mannopyranoside 
• 71526-33-5 methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 

Downstream Products

• 138904-01-5 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 2-pyridinecarboxylate 
• 138904-01-5 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 2-pyridinecarboxylate 
• 92812-56-1 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-4-O-allyl-2,3-di-O-benzyl-α-D-glucopyranoside 
• 82805-19-4 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-4-O-allyl-2,3-di-O-benzyl-α-D-glucopyranoside 
• 83921-84-0 ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 83906-38-1 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 146773-71-9 allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 92052-34-1 O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-dichloracetimidat 
• 92052-34-1 O-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-dichloracetimidat 
• 92414-03-4 Iodo-acetic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 78890-59-2 Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 78890-60-5 Methoxy-acetic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 92052-29-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 
• 92052-30-7 O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) 2,2,2-trifluoroacetimidate 

Relevant articles and documents

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Method for continuously synthesizing benzyl-substituted glucolactone by adopting microchannel reaction device

The invention discloses a method for continuously synthesizing benzyl-substituted glucolactone by adopting a microchannel reaction device. The method comprises the following steps: taking methyl-alpha-D-mannopyranoside as an initial raw material, preparing the methyl-alpha-D-mannopyranoside into an old organic solvent solution, and reacting the old organic solvent solution with an organic solvent solution of benzyl chloride in a first microreactor to generate methyl glucose with hydroxyl protected by benzyl; reacting a homogeneous solution formed by mixing a reaction solution of benzyl-substituted gluconic acid and a small amount of hydrochloric acid solution in a second microreactor for demethylation to generate hydroxyl benzyl-substituted glucose; and finally, reacting the reaction solution with an aqueous solution of hydrogen peroxide and sodium hydroxide and an organic solvent solution of tetramethylpiperidine nitrogen oxide in a third microreactor to generate the high-purity hypoglycemic drug Dapagliflozin intermediate benzyl substituted glucolactone. The method disclosed by the invention is higher in heat and mass transfer efficiency and easier to industrially amplify, the initial materials are simple, cheap and easily available, the process is simple, the obtained intermediate is high in purity and high in yield, the production cost can be effectively reduced, and the method is suitable for industrial production.

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.