89025-46-7

Basic information

• Product Name: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE
• Synonyms: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE;2,3,4,6-tetra-o-benzyl-d-glucopyranosyl fluoride,predominantly α;2,3,4,6-TETRA-O-BENZYL-ALPHA-SS-GLUCOPYRANOSYL FLUORIDE;2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSYL FLUORIDE,PREDOMINANTLY ALPHA;2,3,4,6-Tetra-o-benzyl-alpha--glucopyranosyl fluoride;-D-glucopyranosyl Fluoride;2,3,4,6-Tetra-O-benzyl-α(2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-fluorotetrahydro-2H-pyran
• CAS NO: 89025-46-7
• Molecular Formula: C₃₄H₃₅FO₅
• Molecular Weight: 542.64
• Product Categories: Biochemistry;Glucose;Halogenosugars;Sugars
• Mol File: 89025-46-7.mol
• Article Data: 55

Chemical Properties

• Melting Point: 50-60 °C(lit.)
• Boiling Point: 639.422oC at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.206g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE(89025-46-7)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE(89025-46-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 89025-46-7(Hazardous Substances Data)

Usage

Description

2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE, with the chemical abstracts service number 89025-46-7, is a carbohydrate building block that is highly valuable in the field of organic chemistry and biochemistry. Its unique structure, featuring a fluorine substituent, makes it a versatile and efficient reagent for various glycosylation reactions. The benzyl groups protect the hydroxyl groups, allowing selective reactions to occur at specific sites on the molecule.

Uses

Used in Organic Chemistry:
2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE is used as a carbohydrate building block for the synthesis of complex oligosaccharides and glycoconjugates. Its fluorine substituent enhances the reactivity of the molecule, making it an ideal candidate for various glycosylation reactions.
Used in Biochemistry:
In the field of biochemistry, 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE is used as a glycosyl donor in enzymatic and chemical glycosylation reactions. Its protected structure allows for selective reactions, making it a valuable tool for the synthesis of biologically active glycoconjugates.
Used in Medicinal Chemistry:
2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE is used as a key intermediate in the synthesis of glycoproteins and glycolipids, which play crucial roles in various biological processes, including cell-cell recognition, immune response, and cell signaling. Its ability to participate in glycosylation reactions makes it a valuable asset in the development of new drugs and therapeutic agents.
Used in Material Science:
In material science, 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE is used as a component in the development of advanced materials with specific properties, such as self-assembling systems, drug delivery systems, and biosensors. Its unique structure and reactivity contribute to the creation of innovative materials with potential applications in various industries.
Overall, 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSYL FLUORIDE is a versatile and valuable compound with applications in various fields, including organic chemistry, biochemistry, medicinal chemistry, and material science. Its unique structure and reactivity make it an essential tool for the synthesis of complex carbohydrates and the development of new materials and therapeutic agents.

InChI:InChI=1/C34H35FO5/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/h1-20,30-34H,21-25H2/t30-,31-,32+,33-,34+/m1/s1

Upstream product

• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 220662-68-0 2-{[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy]methyl}benzoic acid 
• 38184-10-0 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 117841-64-2 (pent-4′-enyl) 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 365534-59-4 2'-(benzyloxycarbonyl)benzyl α-D-mannopyranoside 
• 635320-28-4 2-((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 194594-76-8 (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 
• 131531-70-9 4-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 

Downstream Products

• 55094-26-3 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 117894-99-2 methyl (2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 64694-18-4 methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 128745-64-2 2,4-dimethylpentan-3-yl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 128745-65-3 2,4-dimethylpentan-3-yl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 70849-14-8 (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(3S,5S,8R,9S,10S,13R,14S,17R)-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran 
• 70849-14-8 (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(3S,5S,8R,9S,10S,13R,14S,17R)-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran 
• 128820-59-7 cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 128820-60-0 cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 117841-67-5 6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 117841-66-4 6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 128745-67-5 tert-butyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 128745-66-4 tert-butyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 

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.

A dehydrative glycosylation protocol mediated by nonafluorobutanesulfonyl fluoride (NfF)

A new dehydrative glycosylation protocol that proceeds through selective activation of glycosyl hemiacetals with nonafluorobutanesulfonyl fluoride (NfF) has been disclosed. Contrary to the major classical glycosylation reactions that proceed under acidic

Chemical glucosylation of pyridoxine

The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.