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

Description

2,3,4,6-Tetra-O-benzyl-D-glucopyranose, with the CAS number 4132-28-9, is a white crystalline solid that serves as a versatile compound in the field of organic synthesis. It is a derivative of D-glucopyranose, a monosaccharide, where four hydroxyl groups are substituted with benzyl groups at the 2nd, 3rd, 4th, and 6th positions. This modification enhances its reactivity and compatibility with various organic reactions, making it a valuable intermediate in the synthesis of complex organic molecules.

Uses

Used in Organic Synthesis:
2,3,4,6-Tetra-O-benzyl-D-glucopyranose is used as a synthetic intermediate for the preparation of various complex organic molecules. Its benzyl-protected structure allows for selective reactions at specific functional groups, facilitating the synthesis of a wide range of target compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is used as a key building block for the development of novel drug candidates. Its unique structure and reactivity enable the creation of bioactive molecules with potential therapeutic applications.
Used in Chemical Research:
2,3,4,6-Tetra-O-benzyl-D-glucopyranose is also utilized in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methodologies. Its versatile structure allows researchers to explore different reaction pathways and optimize reaction conditions for specific applications.
Used in Material Science:
In the field of material science, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose can be employed as a component in the design and synthesis of advanced materials, such as polymers and dendrimers, with tailored properties for various applications, including drug delivery, sensors, and catalysts.
Overall, 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is a valuable compound with diverse applications in organic synthesis, pharmaceuticals, chemical research, and material science, owing to its unique structure and reactivity.

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

• 13096-63-4 2,3,4,6-Tetra-O-benzyl-N,N-dimethyl-D-gluconamid 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 115969-49-8 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 128785-05-7 Dimethyl-phenyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-silane 
• 74352-41-3 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 134003-35-3 pent-4-enyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 136215-68-4 2,3,4,6,1',3',4'-hepta-O-benzyl-6'-O-tert-(butyldiphenylsilyl)sucrose 
• 139212-74-1 N-sodio-N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazidate 
• 150-76-5 4-methoxy-phenol 
• 6207-45-0 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 
• 78136-20-6 (2R,3S,4S)-2,3,4,6-Tetrakis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexanal 
• 78136-20-6 2,3,4,6-tetra-O-benzyl-5-O-(tert-butyldimethylsilyl)-L-idose 
• 117253-13-1 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 53929-48-9 (2R,3R,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-ol 
• 74024-22-9 2,3:4,5-di-O-isopropylidene-1-O-<2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl>-β-D-fructopyranose 
• 74024-22-9 2,3:4,5-di-O-isopropylidene-1-O-<2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl>-β-D-fructopyranose 
• 139293-33-7 2-((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrimidine 
• 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 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 74808-06-3 O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-N,2,2-triphenylacetimidat 
• 74808-05-2 2,3,4,6-tetra-O-benzyl-1-O-(N-4-methylphenyl)diphenylacetimidyl-β-D-glucopyranose 
• 143542-00-1 2-(2,3,4,6-tetra-O-benzyl-D-glycero-D-gulo-hexitol-1-yl)pyrrole 
• 143542-03-4 2,3,4,6-Tetra-O-benzyl-1,1-dipyrryl-1-deoxy-D-glucitol 
• 92414-02-3 2,3,4,6-tetra-O-benzyl-1-O-bromoacetyl-β-D-glucopyranose 
• 129318-98-5 2,3,4,6-tetra-O-benzyl-1-deoxy-1,1-bis(2-hydroxy-4,5-methylenedioxyphenyl)-D-glucitol 
• 85422-87-3 1-phenyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one 

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.

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.

Synthesis method of voglibose

The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.