132969-99-4

Basic information

• Product Name: 1-(3′,5′-di-O-benzoyl-2′-deoxy-αβ-L-ribofuranosyl)thymine
• CAS NO: 132969-99-4
• Molecular Weight: 450.448
• Mol File: 132969-99-4.mol

Chemical Properties

• CAS DataBase Reference: 1-(3′,5′-di-O-benzoyl-2′-deoxy-αβ-L-ribofuranosyl)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3′,5′-di-O-benzoyl-2′-deoxy-αβ-L-ribofuranosyl)thymine(132969-99-4)
• EPA Substance Registry System: 1-(3′,5′-di-O-benzoyl-2′-deoxy-αβ-L-ribofuranosyl)thymine(132969-99-4)

Safety Data

• Hazardous Substances Data: 132969-99-4(Hazardous Substances Data)

Upstream product

• 175024-33-6 C₂₃H₂₉N₂O₇P 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 65-71-4 thymin 
• 132969-97-2 1-(2-O-Acetyl-3,5-di-O-benzoyl-α-L-arabinofuranosyl)thymine 
• 133008-03-4 1,2-Di-O-acetyl-3,5-di-O-benzoyl-L-arabinofuranose 
• 132969-98-3 C₂₄H₂₂N₂O₈ 
• 108647-88-7 ((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate 
• 95041-53-5 3,5-Di-O-benzoyl-2-desoxy-D-ribose 
• 51255-12-0 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-D-erythro-pentafuranose 
• 3444-09-5 1,3-bis(trimethylsilyl)thymine 

Downstream Products

• 137121-87-0 α/β-D-thymidine 
• 132970-02-6 1-(3'-Azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine 
• 132970-00-4 1-<5-O-(4-Monomethoxytrityl)-2-deoxy-α-L-erythro-pentafuranosyl>thymine 
• 131682-41-2 1-[(2R,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4-dione 

Relevant articles and documents

Synthesis of l -Deoxyribonucleosides from d -Ribose

The preparation of 2-deoxy-l-ribose derivatives or mirror image deoxyribonucleosides (l-deoxyribonucleosides) from d-ribose is reported. Starting from inexpensive d-ribose, an acyclic d-form carbohydrate precursor was synthesized to study a unique carbonyl translocation process. In this novel radical reaction, not only was the configuration of the sugar transformed from the d-form to the l-form, but also deoxygenation at the C(2) position of the sugar was successfully achieved. This is one of the most practical methods for converting a d-sugar to a 2-deoxy-l-sugar in a one-step reaction. To further identify the reaction product, radical reactions followed by treatment with 1,3-propanedithiol and then benzoylation were performed to afford a dithioacetal derivative. The stereochemistry and configuration of the 2-deoxy-l-ribose dithioacetal derivative were confirmed by its X-ray crystal structure. To further apply this methodology, a diethyl thioacetal derivative was formed, followed by selective benzoyl protection, and an NIS-initiated cyclization reaction to give the desired ethyl S-l-2-deoxyriboside, which can be used as a 2-deoxy-l-ribosyl synthon in the formal total synthesis of various l-deoxyribonucleosides, such as l-dT.

N-glycosylation with glycosyl diethyl phosphites: A highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides

A facile and direct method for the construction of 2′-deoxy-β-N-glycosidic linkages in 2′-deoxyribonucleoside synthesis has been developed by using 3-(3,4,5-trimethoxybenzoyl)-protected 2-deoxyribofuranosyl diethyl phosphites as a glycosyl donor in the presence of trimethylsilyl triflate, wherein coupling reactions with silylated pyrimidine bases have been found to exhibit β-selectivities up to 96%.

A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates

A trimethylsilyl triflate-mediated coupling reaction to produce protected 2′-deoxynucleosides has been developed by using N,N,N',N'-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.

SYNTHESIS OF NEW 2'-DEOXY-3'-SUBSTITUTED-α-L-THREO-PENTAFURANONUCLEOSIDES OF THYMINE AS POTENTIAL ANTIVIRAL AGENTS.

The title compounds, which are related to AZT and its congeners have been synthesized by a multi-step approach and their antiviral properties examined.

Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides

2'-Deoxyribonucleosides are regiospecifically synthesized in high yields by catalyzing with KI-dibenzo-18-crown-6 PTC the condensation between unprotected silylated purines and pyrimidines and the appropriate easily available 2-deoxy-ribofuranosyl or pyranosyl sugar derivatives.