4163-40-0

Usage

Uses

Used in Organic Chemistry Research:
2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside is used as a building block for the synthesis of other complex carbohydrate molecules, enabling the manipulation of specific carbohydrate functional groups. Its unique structure makes it a valuable tool for developing new drugs, materials, and biomolecules.
Used in the Study of Glycosylation Reactions:
In the field of glycosylation reactions, 2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside serves as a key component, facilitating the exploration of carbohydrate interactions and the development of novel glycosylation methods.
Used in Drug Development:
2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside is employed as a reagent in drug development, aiding in the discovery and synthesis of new pharmaceutical compounds with potential therapeutic applications.
Used in Biomolecular Research:
2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside is also used in biomolecular research to study the interaction of carbohydrates with enzymes and proteins, providing insights into carbohydrate recognition and function in biological systems.
Used in Material Science:
2,3,4,6-Tetra-O-benzoyl-1-deoxy-1-fluoro-beta-D-glucopyranoside contributes to the field of material science by serving as a component in the development of new materials with unique properties, such as self-assembling systems and responsive materials.

Upstream product

• 125367-09-1 n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 123487-55-8 3,4,6-tri-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) 
• 65236-83-1 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 66888-27-5 penta-O-acetyl-D-mannose 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 950602-83-2 4-methylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 1392228-57-7 tolyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside (R)-S-oxide 
• 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 
• 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 
• 98-88-4 benzoyl chloride 

Downstream Products

• 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 
• 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 
• 1134525-30-6 phenyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 6899-46-3 2,3,4,6-tetra-O-benzoyl-1-O-cyclohexyl-β-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 
• 128503-39-9 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-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 

Relevant academic research and scientific papers

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.

Glycosyl fluorides from n-pentenyl-related glycosyl donors-application to glycosylation strategies

n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga's reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy 2BF4),

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.

Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3?Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.

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-

IPy2BF4/HF-pyridine: A new combination of reagents for the transformation of partially unprotected thioglycosides and n-pentenyl glycosides to glycosyl fluorides

(Chemical Equation Presented) The combination of bis(pyridinium)iodonium (I) tetrafluoroborate (IPy2BF4), and hydrogen fluoride pyridine (HF-py) forms an iodine monofluoride (IF) synthetic equivalent that can be used in the preparati

IPy2BF4-mediated transformation of n-pentenyl glycosides to glycosyl fluorides: A new pair of semiorthogonal glycosyl donors

Bis(pyridinium) iodonium(1) tetrafluoroborate (IPy2BF 4), a solid and stable reagent, can be used to transform n-pentenyl orthoesters (NPOEs) and n-pentenyl glycosides (NPGs) into glycosyl fluorides. The latter pair constitutes a new

Stereospecific α-D-mannosylation

The stereospecific formation of α-D-mannosyl glycosidic linkages has been achieved in high yield using tetra-O-pivaloyl-α-D-mannopyranosyl fluoride and boron trifluoride diethyl etherate in dichloromethane. Examples of the α-D-mannosylation of primary, secondary, benzylic and phenolic hydroxyl groups are described. Copyright (C) 1999 Elsevier Science Ltd.

Glycosylation of Phenols: Preparation of 1,2-cis and 1,2-trans Glycosylated Tyrosine Derivatives to be used in Solid-phase Glycopeptide Synthesis

The synthesis of four building blocks, Nα-Fmoc-Tyr(Ac4-β-D-Glc)-OPfp 6, Nα-Fmoc-Tyr(Bz4-α-D-Glc)-OPfp 16, Nα-Fmoc-Tyr4-α-D-Glc-(1->4)-Ac3-β-D-Glc>-OPfp 9 and Nα-Fmo