4163-40-0

Basic information

• Product Name: 2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside
• Synonyms: 2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside;2,3,4,6-Tetra-O-benzoyl-beta-D-glucopyranosyl fluoride min. 98%;beta-D-Glucopyranosyl fluoride 2,3,4,6-tetrabenzoate
• CAS NO: 4163-40-0
• Molecular Formula: C₃₄H₂₇FO₉
• Molecular Weight: 598.58
• Mol File: 4163-40-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside(4163-40-0)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside(4163-40-0)

Safety Data

• Hazardous Substances Data: 4163-40-0(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside is a synthetic chemical compound that is commonly used in organic chemistry research. It is a derivative of glucose, with the hydroxyl groups at positions 2, 3, 4, and 6 replaced by benzoyl groups, and a fluorine atom replacing the hydroxyl group at position 1. 2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside is often used as a building block for the synthesis of other complex carbohydrate molecules, particularly in the study of glycosylation reactions. Its unique structure allows for the manipulation of specific carbohydrate functional groups, making it a valuable tool for developing new drugs, materials, and biomolecules. Additionally, 2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside is a useful reagent for studying the interaction of carbohydrates with enzymes and proteins.

Upstream product

• 98-88-4 benzoyl chloride 
• 2713-54-4 α-D-mannopyranosyl fluoride 
• 627466-64-2 2,3,4,6-tetra-O-benzoyl-D-glucopyranose 
• 69534-63-0 1,2,3,4,6-penta-O-benzoyl-5-C-bromo-β-D-glucopyranose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose 
• 297747-11-6 (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 1392228-57-7 tolyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside (R)-S-oxide 
• 950602-83-2 4-methylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 65236-82-0 1,2-O-(α-methoxybenzylidene)-3,4,6-tri-O-benzoyl-β-D-mannopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 66888-27-5 penta-O-acetyl-D-mannose 
• 65236-83-1 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 

Downstream Products

• 128503-39-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 128503-40-2 methyl-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 118579-76-3 methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 125135-28-6 methyl 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 128503-39-9 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside 
• 6899-46-3 2,3,4,6-tetra-O-benzoyl-1-O-cyclohexyl-β-D-glucopyranoside 
• 1134525-30-6 phenyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 

Relevant articles and documents

A Substituent-Directed Strategy for the Selective Synthesis of L-Hexoses: An Expeditious Route to L-Idose

L-Hexoses are rare but biologically significant components of various important biomolecules. However, most are prohibitively expensive (if commercially available) which limits their study and biotechnological exploitation. New, efficient methods to access L-hexoses and their derivatives are thus of great interest. In a previous study, we showcased a stereoselective Bu3SnH-mediated transformation of a 5-C-bromo-D-glucuronide to an L-iduronide. We have now drawn inspiration from this result to derive a new methodology – one that can be harnessed to access other L-hexoses. DFT calculations demonstrate that a combination of a β-F at the anomeric position and a methoxycarbonyl substituent at C-6 is key to optimising the selectivity for the L-hexose product. Our investigations have also culminated in the development of the shortest known synthetic route to a derivative of L-idose from a commercially available starting material (45 % yield over 3 steps). Collectively, these results address the profound lack of understanding of how to synthesise L-hexoses in a stereoselective fashion.

Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates

Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion.

Reaction of 1,2-orthoesters with HF-pyridine: A method for the preparation of partly unprotected glycosyl fluorides and their use in saccharide synthesis

Glycosyl fluorides can be prepared In an efficient manner by treatment of pyranose- or furanose-derlved 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method Is compatible with the presence of a variety of protecting groups, including fert-