52783-53-6

Basic information

• Product Name: methyl 3,5-O-di-t-butylsilylene-α-D-arabinofuranoside
• Synonyms: methyl 3,5-O-di-t-butylsilylene-α-D-arabinofuranoside;1-O-Methyl-2,3,5-Tri-O-Benzoly-Beta-D-Ribofuranse
• CAS NO: 52783-53-6
• Molecular Formula: C₂₇H₂₄O₈
• Molecular Weight: 476.48
• EINECS: -0
• Mol File: 52783-53-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 3,5-O-di-t-butylsilylene-α-D-arabinofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3,5-O-di-t-butylsilylene-α-D-arabinofuranoside(52783-53-6)
• EPA Substance Registry System: methyl 3,5-O-di-t-butylsilylene-α-D-arabinofuranoside(52783-53-6)

Safety Data

• Hazardous Substances Data: 52783-53-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl 3,5-O-di-t-butylsilylene-α-D-arabinofuranoside is used as an intermediate in organic synthesis for the preparation of other arabinofuranosides. The protection of hydroxyl groups by t-butylsilylene groups allows for selective reactions and the synthesis of complex molecules with desired properties.
Used in Research and Development:
Methyl 3,5-O-di-t-butylsilylene-α-D-arabinofuranoside is used as a research compound to study the properties and applications of arabinofuranosides. Its stability and reactivity make it a valuable tool for understanding the structure and function of related compounds in various fields, such as pharmaceuticals, materials science, and biochemistry.
Used in Industrial Applications:
Methyl 3,5-O-di-t-butylsilylene-α-D-arabinofuranoside may be used in the development of new materials and products that require the unique properties of arabinofuranosides. Its stability and reactivity can be advantageous in creating innovative solutions for various industries, such as pharmaceuticals, cosmetics, and food additives.

Upstream product

• 67-56-1 methanol 
• 10323-20-3 D-Arabinose 
• 98-88-4 benzoyl chloride 
• 70051-90-0 tri-O-benzoyl-β-D-arabinofuranosyl bromide 
• 4348-68-9 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide 
• 56607-40-0 methyl D-arabinofuranoside 
• 25545-03-3 β-D-arabinofuranose 
• 58510-41-1 di-O-benzoyl-1,2-O-(α-methoxybenzylidene)-α-D-ribofuranose 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 5517-61-3 methyl 3'-O-benzoyl-β-D-apiofuranoside 
• 5517-60-2 methyl 3'-O-benzoyl-2,3-O-isopropylidene-β-D-apiofuranoside 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 51970-31-1 (2R,3R,4S,5R)-2-azido-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 13035-61-5 1,2,3,5-tetraacetylribose 

Downstream Products

• 4348-68-9 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide 
• 502761-66-2 C₁₃H₁₆O₆C₁₄H₈O₂ 
• 57236-69-8 (3S,4R,5R)-2-acetoxy-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 
• 59599-14-3 2,3,5-tetra-O-benzoyl-α-D-arabinofuranosyl chloride 
• 204918-53-6 methyl 2-O-benzoyl-α-D-arabinofuranoside 
• 282107-51-1 Ethyl 2-O-benzoyl-3-O-benzyl-1-thio-α-D-arabinofuranoside 
• 282107-64-6 ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside 
• 282107-63-5 8-methoxycarbonyloctyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside 
• 310880-65-0 ethyl 2-O-benzoyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside 
• 282107-57-7 ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside 
• 310880-39-8 octyl 2-O-benzoyl-α-D-arabinofuranoside 
• 310880-56-9 phenyl 2-O-benzoyl-3-O-benzyl-1-seleno-α-D-arabinofuranoside 
• 310880-47-8 octyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside 
• 310880-58-1 octyl 2-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside 

Relevant articles and documents

Method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose

The invention relates to the field of organic synthesis, in particular to a method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose, which comprises the following steps: mixing D-ribose with methanol and a catalyst, heating to react, neutralizing, and concentrating to obtain a methyl esterification intermediate III; mixing the methyl esterification intermediate III with an organic solvent, 4-dimethylaminopyridine and an acid-binding agent, cooling, dropwise adding benzoyl chloride for reaction, washing with water for layering, and drying to obtain a benzoylated intermediateII; finally, mixing the benzoylated intermediate II with an organic solvent and acetic anhydride, then adding a catalyst, stirring, carrying out heat preservation reaction for 10-20 hours at the temperature of 0-70 DEG C, and after the reaction is qualified, cooling, crystallizing and centrifuging to obtain a crude product; finally, performing recrystallization and centrifugal drying to obtain the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose, and obtaining the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1-beta-D-ribofuranose. The method has the advantages of short reaction steps, high chemicaland optical purity, simple operation, easily available raw materials, low cost, small amount of three wastes, environmental friendliness and the like, and is suitable for industrial production.

2-Hydroxyimino-6-aza-pyrimidine nucleosides: Synthesis, DFT calculations, and antiviral evaluations

The global public health concerns and economic impact caused by emerging outbreaks of RNA viruses call for the search for new direct acting antiviral agents. Herein, we describe the synthesis, DFT calculations, and antiviral evaluation of a series of novel 2-hydroxyimino-6-aza-pyrimidine ribonucleosides. DFT//B3LYP/6-311+G?? calculations of the tautomeric distributions of the 2-hydroxyimino nucleosides 7, 8, and 9 in aqueous environments indicate a predominance of the canonical 2-(E)-hydroxyimino structure, where the hydroxyl group points away from the sugar moiety. The conformer distributions of the latter geometrical isomers of 7, 8, and 9 support the formation of five membered rings via hydrogen bonding between the (E)-C2N-O-H moiety and N3-H of 7 and 8 and between (E)-C2N-O-H and N3 of 9, creating purine shaped nucleosides with the glycosidic linkage at the pyrimidine ring. The newly synthesized nucleosides were screened against an RNA viral panel, of which moderate antiviral activity was observed against Zika virus (ZIKV) and human respiratory syncytial virus (HRSV). 6-Aza-2-hydroxyimino-5-methyluridine derivative 18 showed activity against ZIKV (EC50 3.2 μM), while its peracetylated derivative 19 showed activity against HRSV (EC50 5.2 μM). The corresponding 4-thiono-2-hydroxyimino derivative 8 showed activity against HRSV (EC50 6.1 μM) and against ZIKA (EC50 2.4 μM). This study shows that the 6-aza-2-hydroxyimino-5-methyluracil derived nucleosides can be further optimized to provide potent antiviral agents. This journal is

Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids

An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic α-, keto and methoxy mycolic acids is described.

Magnesium pyrophosphates in enzyme mimics of nucleotide synthases and kinases and in their prebiotic chemistry

Derivatives of ribosyl pyrophosphate have been synthesized, and examined with magnesium salts in the coupling of the ribose unit to various nucleophiles, including pyrazole and 2-chloroimidazole. Only with the magnesium salt present did they generate the ribosyl cation by binding to the leaving group and then couple the ribose derivative with nucleophiles. The role of magnesium salts in phosphorylation of methanol by ATP was also examined. Here a remarkable effect was seen: phosphorylation by ATP was slowed with low concentrations of Mg2+ but accelerated by higher concentrations. Related effects were also seen in the effect of Mg2+ on phosphorylation by ADP. The likely mechanisms explain these effects.

Automated solid phase synthesis of oligoarabinofuranosides

Automated solid phase synthesis enables rapid access to the linear and branched arabinofuranoside oligosaccharides. A simple purification step is sufficient to provide the conjugation ready oligosaccharides in good yield.

Facile synthesis of β- And α-arabinofuranosides and application to cell wall motifs of M. tuberculosis

Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.

Ready preparation of furanosyl n-pentenyl orthoesters from corresponding methyl furanosides

The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam-Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding perbenzoylated pentofuranosyl bromide(s) and then the title compounds.

A one-pot synthesis of 1-α- and 1-β-d-arabinofuranosyl-2- nitroimidazoles: Synthons to the markers of tumor hypoxia

1-α- and 1-β-D-Arabinofuranosyl-2-nitroimidazole (α-AZA and β-AZ A) are synthons for a number of potential markers of tissue hypoxia. A one pot synthesis in which 2-nitroimidazole is coupled with a mixture of α-and β-1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabi

Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazapurine and diketopiperazine

Different arabinosides and ribosides, viz. Ara-DDA or 9(1-β-D- arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-β-D- arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or 1(1-β-D- arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-β-D-

Synthesis and biological evaluation of novel apio nucleosides with thiazole-4-carboxamide and 1,2,4-triazole-3-carboxamide

In view of biological activities of azole nucleosides and apio-dideoxynucleoside, novel apio nucleoside analogues (1 and 2) with thiazole and triazole base moiety were synthesized using 2,3-O-isopropylidene-apio-β -D-furanose (3), which was prepared from D-mannose.