171866-28-7

Basic information

• Product Name: 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose
• Synonyms: 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose
• CAS NO: 171866-28-7
• Molecular Weight: 476.483
• Mol File: 171866-28-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose(171866-28-7)
• EPA Substance Registry System: 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose(171866-28-7)

Safety Data

• Hazardous Substances Data: 171866-28-7(Hazardous Substances Data)

Usage

Molecular Structure

A complex structure derived from ribofuranose, consisting of a ribose sugar molecule with three benzoyl groups and a methyl group attached at specific positions on the sugar ring.

Composition

Composed of a ribose sugar molecule, three benzoyl groups, and a methyl group.

Usage

Commonly used in organic synthesis and as a precursor for the preparation of various pharmaceuticals and biologically active molecules.

Unique Value

Its unique structure and functional groups make it a valuable building block in the development of diverse chemical compounds.

Relevance in Research

Its specific properties and reactivity make it a useful tool for research and development in the field of organic chemistry.

Upstream product

• 98-88-4 benzoyl chloride 
• 162491-62-5 (2S,3R,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol 
• 41546-21-8 L-ribose 
• 95622-16-5 5-O-trityl-D-ribitol 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 7473-38-3 benzyl β-L-arabinopyranoside 
• 55726-00-6 (3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 
• 87-72-9 L-ribose 
• 7296-55-1 L-arabinose 
• 65247-32-7 benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside 
• 26685-74-5 1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose 
• 192133-10-1 Acetic acid (1R,2S)-2,3-diacetoxy-1-((R)-1-acetoxy-2-hydroxy-ethyl)-propyl ester 
• 192133-11-2 L-ribose 2,3,4,5-tetraacetate 

Downstream Products

• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 1173695-22-1 1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-ribofuranose 
• 1748-04-5 (2S,3S,4S,5S)-2-((benzoyloxy)methyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 109923-78-6 6-N-benzoyl-2',3',5'-tri-O-benzoyl-β-L-adenosine 
• 65-46-3 L-cytidine 
• 58-61-7 L-adenosine 
• 171866-29-8 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose 
• 58-96-8 L-uridine 
• 171866-30-1 1,3,5-Tri-O-benzoyl-α-L-ribofuranose 
• 171721-00-9 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranose 
• 171720-99-3 1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose 
• 163252-36-6 clevudine 
• 171721-03-2 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)thymine 
• 179112-78-8 4-N-acetyl-2',3',5'-tri-O-benzoyl-β-L-cytidine 

Relevant articles and documents

A practical synthesis of L-FMAU from L-arabinose

A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-β-L- arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L- Arabinose was convened to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-β-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8% overall yield.

A solid-phase approach to novel purine and nucleoside analogs

This paper describes a method for the preparation of purine analogs using the solid-phase approach. Nucleoside bases were constructed on Merrifield resin by sequential displacement of purine dichloride with amines, and after detachment, the purine analogs were condensed with d,l-ribofuranoside compounds by the Vorbrueggen method. Thereof, l-ribofuranoside was prepared from l-arabinose via the selective oxidation-reduction procedure of the 2-OH group. Some compounds exhibited moderate activity against HIV-1 in PBM cells.

Efficient syntheses of L-ribose and 2-deoxy L-ribose from D-ribose and L-arabinose

Interconversion of the ends of D-ribose 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl bromide 14.