78185-64-5

Basic information

• Product Name: Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside
• Synonyms: Decitabine Impurity 2 (alpha-Isomer);(2R,3S,5R)-5-methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate;Methyl 2-deoxy-alpha-D-erythro-pentofuranoside bis(4-methylbenzoate)
• CAS NO: 78185-64-5
• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.43
• EINECS: -0
• Mol File: 78185-64-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside(78185-64-5)
• EPA Substance Registry System: Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside(78185-64-5)

Safety Data

• Hazardous Substances Data: 78185-64-5(Hazardous Substances Data)

Usage

General Description

Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside is a chemical compound with a complex molecular structure. It is a derivative of ribofuranoside, a type of sugar, and is often used in organic synthesis and research. The addition of toluoyl groups to the sugar molecule makes it more stable and allows for easier manipulation in laboratory settings. Methyl 2-deoxy-3,5-di-O-p-toluoyl-α-D-ribo-furanoside has been utilized in the development of new drugs, as well as in the study of carbohydrate chemistry and biochemistry. Its precise structure and properties make it valuable for a range of scientific applications.

Upstream product

• 533-67-5 2-Deoxy-D-ribose 
• 67-56-1 methanol 
• 452-51-7 D-2-deoxyribose 
• 874-60-2 4-methyl-benzoyl chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 

Downstream Products

• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 871667-92-4 2'-deoxy-5-iodouridine 
• 871664-01-6 5-iodo-2'-deoxy-3',5'-di-O-p-toluoyl-uridine 
• 862100-45-6 5-cyanovinyl-2'-deoxy-5'-dimethoxytrityl-1'α-uridine 

Relevant articles and documents

Preparation of pyridine-stretched 2′-deoxyhypoxanthosine phosphoramidite

Pyridine-stretched 2-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer's sugar (2-deoxy-3,5-di-O-(p-toluoyl)-a-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer's sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2-deoxyadenosine (strA) and pyridine-stretched 2-deoxy-2,6-diaminonebulamine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

Improved Syntheses of Halofuranose Derivatives with the Desired α-Configuration

Chlorination of ribofuranose or 2-deoxyribofuranose derivatives was carried out in a 1,4-dioxane solution of hydrogen chloride. This improved procedure allowed the syntheses of 1-chloro-α-D-ribofuranose and 1-chloro-2-deoxy-α-D-ribofuranose derivatives and offered ease of handling, high yield, and the stereo-controlled α-configuration at C-1.