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

Uses

2,3,4,6-Tetra-O-benzyl-alpha-D-glucopyranosyl Fluoride (cas# 89025-46-7) is a useful carbohydrate building block, due to its fluorine substituent, and is used for glucosylations with activated sulfonium ions, and via photocatalytic glycosylation.

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

• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 100-44-7 benzyl chloride 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 2021-84-3 α-galactosyl fluoride 
• 3866-62-4 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl acetate 
• 53081-25-7 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 

Downstream Products

• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-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 
• 67525-69-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(tert-butoxy)tetrahydro-2H-pyran 
• 78153-80-7 tert-butyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 85422-85-1 1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl cyanide 
• 71119-79-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-ido-heptononitrile 
• 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 
• 56822-48-1 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate 
• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 121820-73-3 phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 72366-52-0 4-phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 

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.