40093-95-6Relevant articles and documents
Synthesis of l -Deoxyribonucleosides from d -Ribose
Song, Wei-Syun,Liu, Si-Xian,Chang, Che-Chien
, p. 14923 - 14932 (2018)
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
Hashimoto, Shun-Ichi,Inagaki, Jun,Sakamoto, Hiroki,Sano, Ai,Nakajima, Makoto
, p. 215 - 220 (2007/10/03)
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%.
Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides
Baud,Chavis,Lucas,Imbach
, p. 4437 - 4440 (2007/10/02)
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.