63593-01-1

Upstream product

• 16053-52-4 threothymidine 
• 50-89-5 thymidine 
• 7791-71-1 5'-O-tritylthymidine 
• 100-44-7 benzyl chloride 

Downstream Products

• 63592-96-1 O^3'-benzyl-5',5'-(N,N'-diphenyl-N,N'-ethane-1,2-diyl-diamino)-5'-deoxy-thymidine 
• 78138-02-0 1-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)thymine 
• 1374508-86-7 C₄₅H₄₈N₆O₁₂ 
• 105038-59-3 {2-[(4-Methoxy-phenyl)-diphenyl-methoxy]-ethyl}-phenyl-phosphoramidic acid 2-chloro-phenyl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 165319-95-9 (3'-O-benzyl-3'-deoxy-β-D-ribo-furanuronic acid)-1-thymine 
• 905435-91-8 5'-O-(2,3-di-O-benzoylpropyl)-N³-benzoyl-3'-O-benzylthymidine 

Relevant academic research and scientific papers

Synthesis of Ribonucleosidic Dimers with an Amide Linkage from D-Xylose

An original and efficient stereocontrolled synthesis of ribonucleosidic homo- and heterodimers has been achieved from inexpensive d-xylose. This successful strategy involved the sequential introduction of nucleobases, using two stereocontrolled N-glycosidation reactions, from a common two-furanoside amide-linked scaffold offering the possibility of obtaining any given base sequence. The pertinence of this approach is illustrated through the preparation of the homodimers UU-34 and TT-35 in 18 steps with an excellent overall yield of more than 10% from d-xylose, while the heterodimer route led to UT-39 in 19 steps with around 10% overall yield.

In search of Flavivirus inhibitors part 2: Tritylated, diphenylmethylated and other alkylated nucleoside analogues

Several flaviviruses, such as the yellow fever virus and the dengue virus cause severe and potentially lethal infection in man. Following up on our initial hit 3′,5′-bistritylated uridine 1, a series of alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against dengue fever virus and yellow fever virus. Hereto, alkyl and aryl groups were attached at various positions of the sugar ring combined with subtle variation of the heterocyclic base. Among the new series of derivatives, 3′,5′-di-O-trityl-5-fluoro-2′-deoxyuridine (39) was the most efficient in this series and inhibited both yellow fever virus and dengue virus replication with a 50% effective concentration (EC50) of ～1 μg/mL without considerable cytotoxicity. The other fluorinated derivatives proved more toxic. Almost all diphenylmethylated pyrimidine nucleosides with 3′,5′-di-O-benzhydryl-2′-deoxyuridine (50) as the example were endowed with strong cytotoxic effects down to 1 μg/mL.

Synthesis and application of a 5′-aldehyde phosphoramidite for covalent attachment of DNA to biomolecules

We recently reported the use of covalently attached DNA as a structural constraint for rational control of macromolecular conformation. Reductive amination was employed to attach each strand of the duplex DNA constraint to RNA, utilizing an aldehyde tethered to the 5′-terminus of the DNA. Here we describe the synthesis of a thymidine phosphoramidite that has the 5′-tethered aldehyde masked as a 1,2-diol. We also describe optimized reductive amination conditions for linking 5′-aldehyde-DNA with 2′-amino-2′-deoxy-RNA. These procedures should be generally applicable for attaching DNA to biomolecules.

Selective cleavage of O-(dimethoxytrityl) protecting group with sodium periodate

Sodium periodate in aqueous organic solvents selectively removes, under mild reaction conditions, the O-(dimethoxytrityl) protecting group. Selectivity of the cleavage was studied using the nucleoside derivatives protected by various types of groups commonly used in nucleoside and nucleotide chemistry.