15397-15-6

Basic information

• Product Name: 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose
• Synonyms: 2-C-Methyl-beta-D-ribofuranose 1,2,3,5-tetrabenzoate;2-C-Methyl-b-D-ribofuranose 1,2,3,5-tetrabenzoate;1,2,3,5-Tetra-O-benzoyl-2...;b-D-Ribofuranose, 2-C-Methyl-, tetrabenzoate;(2S,3R,4R,5R)-5-((benzoyloxy)Methyl)-3-Methyltetrahydrofuran-2,3,4-triyl tribenzoate;2-C-Methyl-1,2,3,5-tetra-O-benzoyl-beta-D-ribofuranose;(2S,3R,4R,5R)-2,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]-3-methyloxolan-3-yl benzoate;1,2,3,5-tera-o-benzoyl-2'-c-methyl-beta-d-ribofuranose
• CAS NO: 15397-15-6
• Molecular Formula: C₃₄H₂₈O₉
• Molecular Weight: 580.586
• EINECS: 1312995-182-4
• Product Categories: Carbohydrates & Derivatives
• Mol File: 15397-15-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 154-156 °C
• Boiling Point: 687.3 °C at 760 mmHg
• Flash Point: 286.7 °C
• Appearance: White to Off-white/Powder
• Density: 1.34
• Vapor Pressure: 9.68E-19mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Soluble in chloroform or acetonitrile
• CAS DataBase Reference: 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose(15397-15-6)
• EPA Substance Registry System: 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose(15397-15-6)

Safety Data

• Hazardous Substances Data: 15397-15-6(Hazardous Substances Data)

Usage

Description

1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose is a white powder compound with the CAS number 15397-15-6. It is primarily used in organic synthesis due to its unique chemical properties.

Uses

Used in Organic Synthesis:
1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose is used as a synthetic building block for the creation of various complex organic molecules. Its unique structure and reactivity make it a valuable compound in the field of organic chemistry, allowing for the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose is used as a key intermediate in the synthesis of certain drugs. Its specific chemical properties enable the development of novel therapeutic agents with improved efficacy and reduced side effects.
Used in Chemical Research:
1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose is also utilized in chemical research to study the properties and reactions of complex organic molecules. Its unique structure provides researchers with valuable insights into the behavior of similar compounds, contributing to the advancement of chemical knowledge and the development of new technologies.

InChI:InChI=1/C34H28O9/c1-34(43-32(38)26-20-12-5-13-21-26)28(41-30(36)24-16-8-3-9-17-24)27(22-39-29(35)23-14-6-2-7-15-23)40-33(34)42-31(37)25-18-10-4-11-19-25/h2-21,27-28,33H,22H2,1H3/t27-,28-,33+,34-/m1/s1

Upstream product

• 75-16-1 methylmagnesium bromide 
• 98-88-4 benzoyl chloride 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 30361-18-3 3,5-dibenzoyloxy-2-C-methy-β-D-ribofuranose 
• 729596-46-7 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone 
• 7392-74-7 (3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate 
• 30361-17-2 2-methyl-2,3,5-tribenzoyl-ribonolactol 
• 492-30-8 2-C-methyl-D-ribono-1,4-lactone 
• 16434-48-3 1,3,5-tri-O-benzoyl-2-C-methyl-α-D-ribofuranose 
• 30361-17-2 2,3,5-tri-O-benzoyl-2-C-methyl-α/β-D-ribofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 2747-38-8 methyltrichlorotitanium 
• 30361-18-3 3,5-di-O-benzoyl-2-C-methyl-D-ribofuranose 

Downstream Products

• 23643-36-9 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine 
• 729595-79-3 (2R,3R,4R,5R)-2-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 622379-84-4 C₃₂H₂₅BrN₄O₇ 
• 622379-55-9 8-(3,4-bis-benzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-4,5-dioxo-3,4,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester 
• 622379-64-0 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine 
• 641571-44-0 (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 
• 892499-45-5 5-amino-3-(2,3,5-tri-O-benzoyl-2-C-methyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2,7(3H,6H)-dione 
• 847550-99-6 4-amino-3-iodo-1-(2-C-methyl-2,3,5-tri-o-benzoyl-β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidine 
• 205171-16-0 (3aR,4S,6R,6aR)-6-[6-(3-Iodo-benzylamino)-purin-9-yl]-2,2,6a-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethyl ester 
• 205171-06-8 2'-Me-CPA 
• 205171-05-7 6-chloro-9-(2-C-methyl-?2-D-ribofuranosyl)-9H-purine 
• 15397-12-3 2'-methyl-adenosine 

Relevant articles and documents

Synthesis process of (2R')-2'-deoxyl-2'-fluoro-2'-methyluridine

The invention discloses a synthesis process of (2R')-2'-deoxyl-2'-fluoro-2'-methyluridine, relates to the technical field of synthesis of medicines, and solves the technical problems of high cost andlow product yield of the existing process. According to the synthesis process, sodium borohydride or potassium borohydride is used for reducing ribose lactone, so that an expensive reductive reagent which is sodium dihydro-bis-(2-methoxyethoxy)aluminate or lithium tri-tert-butoxyaluminum hydride is not used, and the cost is greatly reduced; N,O-bis(trimethylsilyl)acetamide is used as a silicon etherification reagent, so that the yield of glycosylation reaction is increased; the product yield can reach 85-90% and is far higher than that in route III by 58%; the product yield is obviously increased; hydroxyl at the 5' site is protected, so that side reaction in ring-closing reaction can be avoided; meanwhile, a common polar solvent which is dimethylformamide is used; the product yield undercatalysis of sodium hydrogen carbonate can reach 87-92%. The synthesis process is easy to operate; the process condition is more easily controlled; the cost is reduced; the synthesis process is applicable to large-batch production.

Process for the preparation of ribofuranose derivatives

The present invention relates to a new process in 3 steps starting from 2-C-methyl-D-ribopentono-1,4-lactone for the preparation of tetra-acyl ribofuranose derivatives of formula (I): useful in the synthesis of nucleotides.

2′-C-alkylribonucleosides: Design, synthesis, and conformation

Certain 2′-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed. Copyright