154371-07-0

Upstream product

• 50-89-5 thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 

Downstream Products

• 154371-08-1 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-C-methylenethymidine 
• 154371-09-2 1-(2,3-dideoxy-5-O-(4,4'-dimethoxytrityl)-3-C-hydroxymethyl-β-D-threo-pentofuranosyl)thymine 
• 154468-75-4 1-[(2R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 154468-74-3 5'-O-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine 
• 511545-98-5 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphino]-3'-deuterothymidine 
• 186963-82-6 1-{(2R,4R,5R)-4-(Benzenesulfonyl-difluoro-methyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

A deuterated nucleoside phosphoramidite monomer synthesis method

The invention discloses a synthesis method of a deuterium-substituted nucleoside phosphoramidite monomer. According to the technical scheme, the synthesis method of the deuterium-substituted nucleoside phosphoramidite monomer comprises the following steps

NUCLEOSIDE ANALOGUES WHOSE SUGAR MOIETIES ARE BOUND IN S-FORM AND OLIGONUCLEOTIDE DERIVATIVES COMPRISING NUCLEOTIDE ANALOGUES THEREOF

Compounds of the following general formula (1) and salts thereof: where A represents an alkylene group having 1 to 2 carbon atoms, etc.; B represents an aromatic heterocyclic group which may have a substituent, etc.; R1 and R2 each represent a hydrogen atom, a protective group for a hydroxyl group for synthesis of nucleic acid, a phosphate group, or -P(R4)R5 [where R4 and R5 are the same or different, and each represent a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, a mercapto group, a mercapto group protected with a protective group for synthesis of nucleic acid, etc.]; and R3 represents a hydrogen atom, a halogen atom, a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, etc. These compounds are useful for producing oligonucleotide analogues useful for the antisense method, antigene method, etc., and for producing their intermediates.

Stereospecific syntheses of 3'-deuterated pyrimidine nucleosides and their site-specific incorporation into DNA.

[reaction: see text] 2'-Deoxy-3'-deutero pyrimidines have been synthesized in high yields and incorporated into deoxyoligonucleotides using standard phosphoramidite chemistry. A key synthetic step is a stereospecific reduction of 3'-keto nucleosides using sodium triacetoxyborodeuteride to give 3'-deuterated thymidine and 2'-deoxy uridine nucleosides. Conversion of the corresponding phorphoramidites 7a and 7b to 4-triazolo derivatives has, for the first time, enabled incorporation of 2'-deoxy-3'-deutero cytidine and 2'-deoxy-3'-deutero-5-methyl cytidine into oligonucleotides.

3'-C-hydroxymethylthymidine: Synthesis and incorporation into oligodeoxynucleotide analogues

The stereoselective synthesis of 3'-C-hydroxymethylthymidine (5) in five steps from thymidine has been accomplished and this nucleoside has been incorporated into oligodeoxynucleotides (ODNs) in different ways.

Oligodeoxynucleotide analogues containing 3'-deoxy-3'-C-threo-hydroxymethylthymidine: Synthesis, hybridization properties and enzymatic stability

Novel oligodeoxynucleotide analogues containing 3'-C-threo-methylene phosphodiester internucleoside linkages were synthesized on automated DNA-synthesizers using the phosphoramidine approach. The sugar modified phosphoramidite building block 5 was obtaine