139244-35-2

Upstream product

• 4546-72-9 N₆-benzoyl-2'-deoxyadenosine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 91592-96-0 (2R,3S,5R)-5-(6-Amino-purin-9-yl)-2-trimethylsilanyloxymethyl-tetrahydro-furan-3-ol 
• 958-09-8 2'-deoxy-D-adenosine 

Downstream Products

• 858672-62-5 N⁶-benzoyl-9-(5'-O-tert-butyldiphenylsilyl-2'-deoxy-α-D-erythro-pentofuranosyl)adenine 
• 1337976-63-2 C₃₄H₃₈N₅O₆PSi 
• 1337976-45-0 C₄₀H₅₁N₆O₅PSi 
• 195247-31-5 3-N-benzoyl-3'-O-(9-phenylxanthen-9-yl)-2'-deoxyadenosine 
• 140712-79-4 6-N-benzoyl-2'-deoxy-3'-O-dimethoxytrityladenosine 
• 854389-82-5 {(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-ylmethoxymethyl}-phosphonic acid monomethyl ester 
• 3413-66-9 α-deoxyadenosine 
• 858672-59-0 N⁶-benzoyl-9-[3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine 
• 858672-63-6 9-(5'-O-tert-butyldiphenylsilyl-2'-deoxy-α-D-erythro-pentofuranosyl)adenine 
• 58-61-7 adenosine 
• 858672-57-8 N⁶-benzoyl-9-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine 
• 6984-53-8 N⁶,2',3',5'-tetra-O-benzoyladenosine 
• 139244-36-3 N-{9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-oxo-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 
• 221896-00-0 3'-O-<4''-((N-allyloxycarbonyl)-5'''-aminopent-1-yl-oxy)-5''-methoxy-2''-nitrophenylmethoxycarbonyl>-2'-deoxy-5'-O-(tert-butyldiphenylsilyl)-N-6-benzoyladenosine 

Relevant academic research and scientific papers

Effective anomerisation of 2′-deoxyadenosine derivatives during disaccharide nucleoside synthesis

The formation of a disaccharide nucleoside (11) by O3′-glycosylation of 5′-O-protected 2′-deoxyadenosine or its N6-benzoylated derivative has been observed to be accompanied by anomerisation to the corresponding α-anomeric product (12). The latter reaction can be explained by instability of the N-glycosidic bond of purine 2′- deoxynucleosides in the presence of Lewis acids. An independent study on the anomerisation of partly blocked 2′-deoxyadenosine has been carried out. Additionally, transglycosylation has been utilized in the synthesis of 3′-O-β-D-ribofuranosyl-2′-deoxyadenosines and its α-anomer.

Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides

An unique set of 5′-O- and 3′-O-phosphonomethyl derivatives of four natural 2′-deoxyribonucleosides, 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine, 5′-O- and 2′-O-phosphonomethyl derivatives of 1-(3-deoxy-β-D-erythro-pentofuranosyl)thymine, and 1-(3-deoxy-β-D- threo-pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4-methoxy-1-oxido-2-pyridylmethyl ester group, serving also as an intramolecular catalyst in the coupling step.

Solid-phase synthesis of branched RNA and branched DNA/RNA chimeras

An effective method for synthesising branched oligonucleotides on solid phase in the 5' to 3' direction has been developed. Special branch-point monomers enable the synthesis of branched oligonucleotides which can have sequences of different length and base composition attached to the 2'- and 3'-hydroxyl groups of the branch point ribonucleoside. The branched oligonucleotides are assembled on commercial DNA synthesisers, the crude products are readily purified by reversed phase HPLC and the fully deprotected products are conveniently analysed by mass spectrometry.

Ribosylation of pyrimidine 2'-deoxynucleosides

The previously developed method for the preparation of 2'-O-D- ribofuranosyl-nucleosides is extended to ribosylation of 2'- deoxynucleosides. The scope and limitations of this reaction are discussed.