79083-29-7

Basic information

• Product Name: (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran
• Synonyms: (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran
• CAS NO: 79083-29-7
• Molecular Weight: 434.532
• Mol File: 79083-29-7.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran(79083-29-7)
• EPA Substance Registry System: (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran(79083-29-7)

Safety Data

• Hazardous Substances Data: 79083-29-7(Hazardous Substances Data)

Usage

Description

(2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran is a complex organic compound characterized by its tetrahydrofuran ring with multiple benzyl and methoxy groups attached. (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran's stereochemistry, with a 2R, 3R, 4R, 5S configuration, specifies the precise arrangement of substituents around the tetrahydrofuran ring. This unique structure and stereochemistry suggest potential applications in organic synthesis, medicinal chemistry, and as a building block for more complex molecules, making it a subject of interest for further research and development in various chemical and pharmaceutical fields.

Uses

Used in Organic Synthesis:
(2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran serves as a valuable intermediate in organic synthesis due to its unique structure and multiple functional groups. It can be utilized to create a variety of complex organic molecules for different applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran can be employed as a key component in the development of new pharmaceuticals. Its specific stereochemistry and functional groups may contribute to the design of novel drugs with improved efficacy and selectivity.
Used as a Building Block for Complex Molecules:
(2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran's intricate structure positions it as a potential building block for the synthesis of more complex molecules with diverse applications. Its use in this capacity can lead to the creation of advanced materials and compounds for various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
(2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran is also used in research and development settings to explore its chemical properties, reactivity, and potential interactions with other molecules. This research can lead to a better understanding of its applications and the discovery of new uses in various chemical and pharmaceutical processes.

Upstream product

• 67737-48-8 methyl 5-benzyloxy-β-D-ribofuranoside 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 67737-49-9 methyl 5-O-benzyl-α-D-ribofuranoside 
• 532-20-7 D-Ribose 
• 52485-92-4 methyl α-D-ribofuranoside 
• 1824-96-0 methyl ribofuranoside 
• 86883-41-2 2,3,5-tri-O-benzyl-α-D-ribofuranosyl fluoride 
• 1825-61-2 Trimethylmethoxysilane 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 917-64-6 methyl magnesium iodide 
• 67-56-1 methanol 

Downstream Products

• 79064-00-9 (2R,3R,4S)-1,3,4-Tris-benzyloxy-5-methoxy-hexan-2-ol 
• 491-19-0 1,4-anhydro-D-ribitol 
• 149118-07-0 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-phenylsulfanyl-tetrahydro-furan 
• 80795-53-5 (2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol 
• 885592-69-8 (2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one 
• 1439900-71-6 (Z)-N-((2S,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-ylidene)-2-methylpropane-2-sulfinamide 
• 107961-03-5 β-1-deoxy-1-C-(phenylthio)-2,3,5-tri-O-benzyl-D-ribofuranose 
• 107961-04-6 α-1-deoxy-1-C-(phenylthio)-2,3,5-tri-O-benzyl-D-ribofuranose 
• 1428321-46-3 (1R,2R,3R,4R)-2,3,5-tris(benzyloxy)-1-methoxy-1-(phenylthio)pentan-4-ol 
• 1439900-72-7 N-((2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-yl)-2-methylpropane-2-sulfinamide 
• 1403250-97-4 (2S)-isopropyl 2-(((((2R,3S,4R,5R)-4-amino-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1439900-80-7 (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate 
• 1439900-77-2 1-((2R,3R,4S,5R)-3-amino-4-(benzyloxy)-5-((benzyloxy)methyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 1439900-76-1 N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide 

Relevant articles and documents

HCV POLYMERASE INHIBITORS

The invention provides compounds of the formula:(I) which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

Anodic coupling reactions and the synthesis of C-glycosides

A convenient, two-step procedure has been developed for converting sugar derivatives into C-glycosides containing a masked aldehyde functional group. The chemistry takes advantage of an anodic coupling reaction between an electron-rich olefin and an alcohol. The sequence works for the formation of both furanose and pyranose derivatives if less polarized vinyl sulfide derived radical cation intermediates are used. With more polarized enol ether derived radical cations, the cyclizations work best for the formation of furanose derivatives where the rate of five-membered ring formation precludes elimination reactions triggered by the radical cation.

Synthesis of β-D-ribofuranosyl-(1→3)-α-L-rhamnopyranose by in situ activating glycosylation using 1-OH sugar derivative and Me3SiBr-CoBr2-Bu4NBr-molecular sieves 4A system

Β-D-Ribofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)- L-rhamnopyranose, the trisaccharide repeating unit of the C. freundii O28, 1c O-specific polysaccharide, was synthesized using in situ activating glycosylation of the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivatives of methyl, allyl, and benzyl α-L-rhamnosides.