4330-34-1

Basic information

• Product Name: METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-*RIB OFURANOSIDE
• Synonyms: METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-*RIB OFURANOSIDE;methyl 2-deoxy-3,5-di-O-P-toluoyl-D-*ribofuranosi;Methyl2-deoxy-3,5-di-O-toluoyl-D-ribofuranoside;2-hydroxy-2-((2R,3S)-3-hydroxy-5-methoxy-3-(2-methylbenzoyl)tetrahydrofuran-2-yl)-1-o-tolylethanone;Methyl 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranoside;Methyl 2-Deoxy-D-erythro-pentofuranoside 4,6-Bis(4-Methylbenzoate);Methyl 2-Deoxy-D-erythro-pentofuranoside Di-p-toluate;D-erythro-Pentofuranoside, Methyl 2-deoxy-, 4,6-bis(4-Methylbenzoate)
• CAS NO: 4330-34-1
• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.42
• Product Categories: Carbohydrates & Derivatives
• Mol File: 4330-34-1.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• Refractive Index: 1.569
• Storage Temp.: −20°C
• CAS DataBase Reference: METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-*RIB OFURANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-*RIB OFURANOSIDE(4330-34-1)
• EPA Substance Registry System: METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-*RIB OFURANOSIDE(4330-34-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4330-34-1(Hazardous Substances Data)

Usage

Description

METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-RIB OFURANOSIDE, also known as Methyl 2-Deoxy-3,5-di-O-p-toluoyl-D-erythro-pentoside (CAS# 4330-34-1), is a chemical compound that is characterized by its pale brown oil appearance. It is primarily used in the field of organic synthesis, where it serves as a valuable intermediate or building block for the creation of more complex molecules.

Uses

Used in Organic Synthesis:
METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-RIB OFURANOSIDE is used as a synthetic intermediate for the development of various complex organic molecules. Its unique chemical structure allows it to be a versatile component in the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-RIB OFURANOSIDE is used as a key component in the synthesis of novel drug candidates. Its incorporation into these molecules can potentially enhance their pharmacological properties, such as potency, selectivity, and bioavailability, leading to more effective treatments for various diseases and conditions.
Used in Agrochemical Industry:
METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-RIB OFURANOSIDE is also utilized in the agrochemical industry for the development of new pesticides, herbicides, and other crop protection agents. Its unique chemical properties can contribute to the creation of more effective and environmentally friendly products that can help improve crop yields and protect against various pests and diseases.
Used in Specialty Chemicals Industry:
In the specialty chemicals industry, METHYL 2-DEOXY-3,5-DI-O-P-TOLUOYL-D-RIB OFURANOSIDE is employed as a building block for the synthesis of various specialty chemicals, such as additives, coatings, and materials with unique properties. Its incorporation into these products can lead to improved performance, durability, and functionality, making them more valuable in their respective applications.

InChI:InChI=1/C22H24O6/c1-14-8-4-6-10-16(14)21(23)26-13-19-18(12-20(25-3)27-19)28-22(24)17-11-7-5-9-15(17)2/h4-11,18-20H,12-13H2,1-3H3/t18-,19+,20?/m0/s1

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 22900-10-3 2-deoxy-D-ribose 
• 452-51-7 D-2-deoxyribose 
• 13222-85-0 p-methylbenzoic anhydride 

Downstream Products

• 4449-38-1 2'-deoxy-3',5'-di-O-(4-methylbenzoyl)uridine 
• 4449-37-0 1-[O³,O⁵-bis-(4-methyl-benzoyl)-α-D-erythro-2-deoxy-pentofuranosyl]-1H-pyrimidine-2,4-dione 
• 68753-36-6 1-<2'-Desoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl>-2(1H)-pyrimidinon 
• 3601-89-6 Hoffer's chlorosugar 
• 830346-85-5 C₄₁H₃₂O₅ 
• 790710-34-8 3-perylene-1'-α-D-2'-deoxyriboside-3',5'-di(p-toluoyl) ester 
• 864156-05-8 2-amino-3-benzyl-7-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one 
• 180854-12-0 ((2R,3R,5R)-3-((4-methylbenzoyl)oxy)-5-(pyren-1-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate 
• 180737-30-8 ((2R,3R)-3-((4-methylbenzoyl)oxy)-5-(pyren-1-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate 

Relevant articles and documents

Synthesis method of desicitabine intermediate alpha-substituted deoxyribose

The invention provides a synthesis method of desicitabine intermediate alpha-substituted deoxyribose. The synthesis route is as follows: R refers to p-methyl benzoyl and X refers to chlorine atomin according to the formula 3 and the formula I. The synthesis method includes the following steps: 1) methylation reaction: a compound of formula 1 is reacted with methyl alcohol under acid catalysis to obtain a compound of the formula 2; 2) acylation reaction: the compound of the formula 2 is dissolved in an organic solvent and reacted with p-methyl benzoyl chloride under alkali catalysis to obtain acompound of the formula 3; 3) chlorination reaction: acetyl chloride is used to adjust the pH value of the acylation reaction solution at low temperature, the acylation reaction solution is filtered,is added with a low polar solvent A, and then is added with acetic acid solution of hydrogen chloride to react to obtain a compound of formula I. The synthesis method uses p-methyl benzoyl as a protective group in the process of synthesizing dicitabine key intermediate to substitute for deoxyribose, and controls the chlorination reaction conditions to obtain high purity alpha-substituted deoxyribose, the high purity alpha-substituted deoxyribose is conducive to coupling with silylation-protected 5-azacytidine to obtain high proportion of beta / alpha, and the dicitabine yield rate is increased.

Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chlorosugar

We are reporting a regioselective and stereoselective route to N2-β-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The SN2 substitution reaction at the anomeric center of Hoffer's chlorosugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chlorosugar with very good yield. The stereoelectronic and steric effects play a crucial role for the observed outcome which is also supported from a theoretical (DFT) study. The methodology is simple, eco-compatible and the tetrazolyl unnatural nucleosides might find applications in decorating DNA for various biotechnological and DNA based material science applications.

Triazolyl donor/acceptor chromophore decorated unnatural nucleosides and oligonucleotides with duplex stability comparable to that of a natural adenine/thymine pair

We report the design and synthesis of triazolyl donor/acceptor unnatural nucleosides via click chemistry and studies on the duplex stabilization of DNA containing two such new nucleosides. The observed duplex stabilization among the self-pair/heteropair has been found to be comparable to that of a natural A/T pair. Our observations on the comparable duplex stabilization has been explained on the basis of possible π-π stacking and/or charge transfer interactions between the pairing partners. The evidence of ground-state charge transfer complexation came from the UV-vis spectra and the static quenching of fluorescence in a heteropair. We have also exploited one of our unnatural DNAs in stabilizing abasic DNA.