162118-38-9

Basic information

• Product Name: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol
• Synonyms: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol
• CAS NO: 162118-38-9
• Molecular Weight: 434.532
• Mol File: 162118-38-9.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol(162118-38-9)
• EPA Substance Registry System: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol(162118-38-9)

Safety Data

• Hazardous Substances Data: 162118-38-9(Hazardous Substances Data)

Upstream product

• 127061-10-3 phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 139684-68-7 C₃₄H₃₆O₅ 
• 169532-17-6 ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside 
• 1256778-82-1 allyl 2-acetamido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 100-44-7 benzyl chloride 
• 127874-75-3 2-methoxyethyl 2,3,4-tri-O-acetyl-β-L-fucopyranoside 
• 73-34-7 6-deoxy-L-galactose 
• 183875-25-4 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 
• 146815-26-1 1-O-acetyl-2,3,4-tri-O-benzyl-β-L-fucopyranose 
• 210035-64-6 (2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2,6-dimethyl-benzenesulfinyl)-6-methyl-tetrahydro-pyran 
• 116514-50-2 ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 87908-23-4 2-methoxyethyl 2,3,4-tri-O-benzyl-β-L-fucopyranoside 

Downstream Products

• 126330-69-6 2-((3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-pyridine 
• 1289154-21-7 (-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside 
• 1352718-49-0 methyl 2,3-di-O-methyl-6-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1352718-48-9 methyl 2,3-di-O-methyl-4-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 153659-02-0 Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite 
• 83562-59-8 1-O-acetyl-2,3,4-tri-O-benzyl-α-L-fucopyranose 

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.

Synthesis of Unprecedented Sulfonylated Phosphono-exo-Glycals Designed as Inhibitors of the Three Mycobacterial Galactofuranose Processing Enzymes

This study reports a new methodology to synthesize exo-glycals bearing both a sulfone and a phosphonate. This synthetic strategy provides a way to generate exo-glycals displaying two electron-withdrawing groups and was applied to eight different carbohydrates from the furanose and pyranose series. The Z/E configurations of these tetrasubstituted enol ethers could be ascertained using NMR spectroscopic techniques. Deprotection of an exo-glycal followed by an UMP (uridine monophosphate) coupling generated two new UDP (uridine diphosphate)-galactofuranose analogues. These two Z/E isomers were evaluated as inhibitors of UGM, GlfT1, and GlfT2, the three mycobacterial galactofuranose processing enzymes. Molecule 46-(E) is the first characterized inhibitor of GlfT1 reported to date and was also found to efficiently inhibit UGM in a reversible manner. Interestingly, GlfT2 showed a better affinity for the (Z) isomer. The three enzymes studied in the present work are not only interesting because, mechanistically, they are still the topic of intense investigations, but also because they constitute very important targets for the development of novel antimycobacterial agents.

C-Glycosyl amino acids through hydroboration-cross-coupling of exo-glycals and their application in automated solid-phase synthesis

O-Glycosylation is one of the most important post-translational modifications of proteins. The attachment of carbohydrates to the peptide backbone influences the conformation as well as the solubility of the conjugates and can even be essential for binding to specific ligands in cell-cell interactions or for active transport over membranes. This makes glycopeptides an interesting class of compounds for medical applications. To enhance the long-term availability of these molecules in vivo, the stabilization of the glycosidic bond between the amino acid residue and the carbohydrate is of interest. The described modular approach affords β-linked C-glycosyl amino acids by a sequence of Petasis olefination of glyconolactones, stereoselective hydroboration and a mild B-alkyl-Suzuki coupling reaction. The coupling products were transformed to C-glycosyl amino acid building-blocks suitable for solid-phase synthesis and successfully incorporated into a partial sequence of the tumor-associated MUC1-glycopeptide. The resulting C-glycopeptides are candidates for the development of long-term stable mimics of O-glycopeptide vaccines. Copyright