94898-42-7

Basic information

• Product Name: 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride
• Synonyms: 2,3,4,6-Tetrakis-O-(phenylMethyl)-α-D-Mannopyranosyl Fluoride
• CAS NO: 94898-42-7
• Molecular Formula: C₃₄H₃₅FO₅
• Molecular Weight: 0
• Product Categories: Aromatics;Carbohydrates & Derivatives
• Mol File: 94898-42-7.mol
• Article Data: 33

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride(94898-42-7)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride(94898-42-7)

Safety Data

• Hazardous Substances Data: 94898-42-7(Hazardous Substances Data)

Usage

Description

2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride, with the chemical formula C27H29FO5 and CAS number 94898-42-7, is a synthetic compound derived from D-mannose, a monosaccharide. It is characterized by the presence of four benzyl groups attached to the hydroxyl groups at the 2, 3, 4, and 6 positions, and a fluorine atom at the anomeric position. This modification enhances its reactivity and stability, making it a valuable intermediate in organic synthesis.

Uses

Used in Organic Synthesis:
2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride is used as a key intermediate in organic synthesis for the preparation of various complex carbohydrates, glycoconjugates, and bioactive compounds. Its benzyl-protected structure allows for selective reactions and subsequent deprotection steps, facilitating the synthesis of target molecules with desired functional groups and stereochemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride is used as a building block for the synthesis of glycoproteins, glycolipids, and other carbohydrate-based drugs. These glycoconjugates play crucial roles in various biological processes, such as cell recognition, signaling, and immune response. 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride's versatility enables the development of novel therapeutic agents with improved efficacy and selectivity.
Used in Material Science:
2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride is also utilized in material science for the fabrication of carbohydrate-based materials, such as hydrogels, nanoparticles, and surfaces. These materials exhibit unique properties, such as stimuli-responsive behavior, biocompatibility, and specific molecular recognition, which can be applied in drug delivery, tissue engineering, and biosensing applications.
Used in Analytical Chemistry:
In analytical chemistry, 2,3,4,6-Tetra-O-benzyl-D-mannopyranosylfluoride serves as a reference compound for the development and validation of analytical methods for the detection and quantification of carbohydrates and their derivatives. Its well-defined structure and reactivity make it an ideal standard for calibration and quality control in various chromatographic and spectroscopic techniques.

Upstream product

• 38184-10-0 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 100-39-0 benzyl bromide 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 74801-29-9 phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 53081-25-7 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 108-93-0 cyclohexanol 
• 744246-05-7 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 

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 
• 129894-49-1 cyclohexyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 129894-48-0 cyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 121820-73-3 phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 116113-70-3 isopropyl-O-2,3,4,6-tetra-O-benzyl-β-D-mannopyranose 
• 116113-69-0 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-isopropoxytetrahydro-2H-pyran 
• 270087-58-6 (2'S,3'S) 6-O-tert-butyldiphenylsilyl-3-O,4-O-[2',3'-dimethoxybutan-2',3'-diyl]-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl fluoride 
• 1259504-73-8 C₄₀H₄₆O₅ 
• 1260083-96-2 C₄₂H₄₂O₅ 
• 1259504-67-0 C₄₀H₄₄O₅ 
• 219864-03-6 trimethyl(((35,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)ethynyl)silane 

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.

Blue Light Photocatalytic Glycosylation without Electrophilic Additives

Photocatalytic formation of glycosidic bonds employing stable and readily accessible O-glycosyl derivatives of 2,2,6,6-tetramethylpiperidin-1-ol is presented that employs an iridium-based photocatalyst and blue LEDs. The reaction proceeds at room temperature and in the absence of additives other than 4 ? molecular sieves. Stereoselectivities are modest but nevertheless dependent on the anomeric configuration of the donor, suggesting a substantial degree of concerted character.

MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS

The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula (I). The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.