40093-95-6

Upstream product

• 51255-12-0 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-D-erythro-pentafuranose 
• 3444-09-5 1,3-bis(trimethylsilyl)thymine 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 108647-88-7 ((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate 
• 75-24-1 trimethylaluminum 
• 258529-69-0 3',5'-dibenzoyloxy-2'-deoxy-5-iodouridine 
• 817622-19-8 C₂₄H₂₁ClN₂O₇ 
• 817622-08-5 C₂₄H₂₀N₂O₇ 
• 95041-53-5 3,5-Di-O-benzoyl-2-desoxy-D-ribose 
• 175024-33-6 C₂₃H₂₉N₂O₇P 

Downstream Products

• 50-89-5 C₁₀H₁₄N₂O₅ 
• 137121-87-0 α/β-D-thymidine 

Relevant academic research and scientific papers

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.

Synthesis of beta-L-2'-deoxy nucleosides

An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

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.

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.