250708-41-9

Upstream product

• 100-39-0 benzyl bromide 
• 250708-42-0 5-azido-3-O-benzyl-4-[(benzyloxy)methyl]-5-deoxy-1,2-O-(1-methylethylidene)-β-L-lyxofuranose 
• 263547-07-5 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(trifluoromethylsulfonyl)-β-L-lyxofuranose 
• 65-71-4 thymin 
• 250708-49-7 1,2-di-O-acetyl-5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-β-L-lyxofuranose 
• 65-71-4 2,4-dihydroxy-5-methylpyrimidine 

Downstream Products

• 1400815-01-1 2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine 
• 1400815-02-2 4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)-2’-O-methylthymidine 
• 250708-38-4 1-{5-deoxy-4-C-{[(4,4'-dimethoxytrityl)oxy]methyl}-2-O-methyl-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine 
• 250708-48-6 1-{2,5-dideoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine 
• 250708-39-5 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-[(trifluoromethyl)sulfonyl]-α-L-xylofuranosyl}thymine 
• 250708-46-4 1-{3-O-benzyl-4-C-[(benzyloxy)methyl]-2,5-dideoxy-2-fluoro-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine 
• 250708-40-8 1-{3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine 
• 263547-13-3 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-(methylsulfonyl)-α-L-lyxofuranosyl}thymine 
• 250708-45-3 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-2,5-dideoxy-2-fluoro-α-L-lyxofuranosyl}thymine 
• 250708-44-2 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}thymine 
• 250708-33-9 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-α-L-xylofuranosyl}thymine 
• 250708-47-5 1-{5-amino-3-O-benzyl-4-C-[(benzyloxy)methyl]-2,5-dideoxy-2-fluoro-α-L-lyxofuranosyl}thymine 

Relevant academic research and scientific papers

Oligonucleotides containing 4'-C-aminomethyl-2'-modified thymidines show increased binding affinity towards DNA and RNA

Oligonucleotides containing 4'-C-aminomethyl-2'-O-methyl or 4'-C-aminomethyl-2'-deoxy-2'-fluoro modified thymidines have been synthesized. Compared with the corresponding oligodeoxynucleotide reference these novel oligonucleotide analogues display increased binding affinity towards complementary single stranded DNA as well as RNA. The possible effect of the positively charged 4'-C-aminomethyl group has been investigated.

CROSSLINKED NUCLEIC ACID GUNA, METHOD FOR PRODUCING SAME, AND INTERMEDIATE COMPOUND

The present invention provides a method for producing guanidine crosslinked artificial nucleic acid (abbreviated hereinafter as GuNA), and an intermediate compound for the production thereof. Specifically, the present invention provides a method for producing a compound represented by general formula I: (in the formula, R1, R2, R3, R4, R5, R6, m and ring A are as defined in the specification) or a salt thereof wherein a reducing agent is reacted with a compound represented by general formula II: (in the formula, R1, R2, R3, R4, R5, R6, m, and ring A′ are as defined in the specification).

Oligonucleotides containing novel 4'-C- or 3'-C-(aminoalkyl)-branched thymidines

The synthesis of four novel 3'-C-branched and 4'-C-branched nucleosides and their transformation into the corresponding 3'-O-phosphoramidite building blocks for automated oligonucleotide synthesis is reported. The 4'-C-branched key intermediate 11 was synthesized by a convergent strategy and converted to its 2-O-methyl and 2'-deoxy-2'-fluoro derivatives, leading to the preparation of novel oligonucleotide analogues containing 4'-C-(aminomethyl)-2'-O-methyl monomer X and 4'-C-(aminomethyl)-2'-deoxy-2'-fluoro monomer Y (Schemes 2 and 3). In general, increased binding affinity towards complementary single- stranded DNA and RNA was obtained with these analogues compared to the unmodified references (Table 1). The presence of monomer X or monomer Y in a 2'-O-methyl-RNA oligonucleotide had a negative effect on the binding affinity of the 2'-O-methyl-RNA oligonucleotide towards DNA and RNA. Starting from the 3'-C-allyl derivative 28, 3'-C-(3-aminopropyl)-protected nucleosides and 3'- O-phosphoramidite derivatives were synthesized, leading to novel oligonucleotide analogues containing 3'-C-(3-aminopropyl)thymidine monomer Z or the corresponding 3'-C-(3-aminopropyl)-2'-O,5-dimethyluridine monomer W (Schemes 4 and 5). Incorporation of the 2'-deoxy monomer Z induced no significant changes in the binding affinity towards DNA but decreased binding affinity towards RNA, while the 2'-O-methyl monomer Z induced decreased binding affinity towards DNA as well as RNA complements (Table 2).