151767-35-0

Usage

Uses

Used in Pharmaceutical Industry:
Methyl-2-deoxy-D-ribofuranoside diacetate is used as a reactant for the synthesis of deoxyribose-related disaccharide nucleosides and their phosphoramidites. These synthesized compounds are essential in the development of new drugs and therapies, particularly in the field of molecular biology and genetics.
Used in Chemical Synthesis:
Methyl-2-deoxy-D-ribofuranoside diacetate is used as a key intermediate in the synthesis of various complex organic molecules, including those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its unique structure and reactivity make it a valuable building block for the creation of novel compounds with diverse properties and functions.
Used in Research and Development:
In academic and industrial research settings, Methyl-2-deoxy-D-ribofuranoside diacetate is utilized as a starting material for the exploration of new chemical reactions and the development of innovative synthetic methods. Its use in research can lead to the discovery of new compounds with potential applications in various fields, including medicine, agriculture, and materials science.

InChI:InChI=1/C6H11O4.2C2H4O2/c1-9-4-2-6(8)10-5(4)3-7;2*1-2(3)4/h4-7H,2-3H2,1H3;2*1H3,(H,3,4)/q-1;;/p-2/t4-,5+,6?;;/m0../s1

Upstream product

• 67-56-1 methanol 
• 533-67-5 2-Deoxy-D-ribose 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 452-51-7 D-2-deoxyribose 

Downstream Products

• 151767-36-1 Acetic acid (2R,3S)-2-acetoxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-yl ester 
• 187165-09-9 7-{(2S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1,7-dihydro-purin-6-one 
• 169105-21-9 ((2R,3S)-3-Benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-yl)-methanol 
• 152696-75-8 2-((2R,3S)-3-Benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-pyrimidine 
• 1254186-96-3 1-(3,5-di-O-acetyl-2-deoxy-D-ribofuranosyl)-5-azacytosine 
• 22432-93-5 4-amino-1-(O³,O⁵-diacetyl-β-D-erythro-2-deoxy-pentofuranosyl)-1H-[1,3,5]triazin-2-one 
• 4594-52-9 1,3,5-tri-O-acetyl-2-deoxyribose 
• 108711-80-4 5-(2,2-difluorovinyl)-2'-deoxyuridine 
• 434936-88-6 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one 
• 434936-89-7 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-α-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one 

Relevant academic research and scientific papers

Open-Close Strategy toward the Organocatalytic Generation of 2-Deoxyribosyl Oxocarbenium Ions: Pyrrolidine-Salt-Catalyzed Synthesis of 2-Deoxyribofuranosides

The reaction of secondary amine salts with 2-deoxy-ribofuranoses under forcible conditions leads to the putative furanosyl oxocarbenium ion that is trapped with various alcohols to provide 2-deoxy-ribofuranosides. The observed anomeric selectivities range from an equimolar mixture to complete α-selectivity in the case of bulky sugar acceptors. Owing to the mechanism and temperature of the transformation, the generated oxocarbenium ion shows little or no facial preference towards the nucleophilic attack of non-carbohydrate acceptors and leads to a mixture of anomers in the case of benzyl and acetyl protected donors. However, the conformationally less flexible tetraisopropylsilyl protected donor reacted with both sugar and non-sugar acceptors in a stereoselective fashion. Besides, the glycosylation with 2-cyanoethanol gave the product with unexpected beta-selectivity presumably due to nitrile effect. The operationally simple organocatalytic protocol provides easy access to otherwise difficult 2-deoxy-ribofuranosides/disaccharides.

Synthesis of 2-deoxy ribose related disaccharide nucleoside and its phosphoramidite

Synthesis of impurity reference compound of anti-tumor drug ISIS 183750 was achieved. In this process, a general method for synthesis of 2-deoxy ribosyl disaccharide nucleosides was established for the first time.

PROCESS FOR THE PREPARATION OF (2R.3S)-2-(HYDROXYMETHYL) -5-METHOXYTETRAHYDROFURAN-3-OL AND ACETYLATED DERIVATIVES THEREOF, FREE OF PYRANOSE COMPOUNDS

A method of preparing a ribofuranose derivative essentially free of pyranose compounds includes a step of contacting a solution of MDR containing MDRP as an impurity in a solvent including methanol and/or tetrahydrofuran with at least one alkali metal periodate under conditions sufficient to oxidize at least a portion of the MDRP. MDR containing at most 5 wt% of MDRP based on the total weight of MDR and MDRP may be produced.

PREPARATION OF DECITABINE

The present application relates to processes for the preparation and purification of decitabine, and to processes for the preparation of a crystalline form of decitabine.

Indium-Mediated Allylation of Aldehydes: A Convenient Route to 2-Deoxy and 2,6-Dideoxy Carbohydrates

The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity.Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated.The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.

Stereocontrolled Synthesis of β-D-2'-Deoxyribonucleosides by Intramolecular Glycosylation

Intramolecular glycosylation of phenyl 2-deoxy-5-O-(2-pyridyl)- and 2-deoxy-5-O-(4-methoxy-2-pyrimidyl)-1-thio-D-ribofuranoside by activation with dimethyl(methylthio)sulfonium tetrafluoroborate followed by hydrolysis gave the corresponding β-2'-deoxyribo

Synthesis and biological activity of 5-(2,2-difluorovinyl)-2'-deoxyuridine

5-(2,2-Difluorovinyl)uracil (IV) was synthesized from 2,4-dimethoxy-5-bromopyrimidine by sequential formylation, difluoromethylenation, and removal of the 2- and 4-methyl groups. Condensation of the trimethylsilyl derivative of IV with protected D-erythro-pentofuranosyl chloride followed by separation of anomers and deblocking gave 5-(2,2-difluorovinyl)-2'-deoxyuridine (V). Compound V was active against herpes simplex virus type 1 (HSV-1) infection as well as tumor cells transformed by the HSV-1 thymidine kinase gene.