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

Chemical Properties

Pale Brown Oil

Uses

Methyl 2-Deoxy-3,5-di-O-p-toluoyl-D-erythro-pentoside (cas# 4330-34-1) is a compound useful in organic synthesis.

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

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

Downstream Products

• 151559-59-0 (Z)-1-<2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl>-5-(1-naphthylmethylene)-2,4-imidazolidinedione 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 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 
• 146039-02-3 N⁶-benzoyl-β-2'-deoxy-3',5'-di-O-p-toluoyladenosine 
• 146039-01-2 N⁶-benzoyl-α-2'-deoxy-3',5'-di-O-p-toluoyladenosine 
• 115945-82-9 1,2-dideoxy-3,5-di-O-p-toluoyl-D-ribose diethyl dithioacetal 

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.