7177-84-6

Upstream product

• 104579-21-7 Phosphoric acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2,6-dichloro-phenyl ester 2-pyridin-2-yl-ethyl ester 
• 497070-24-3 3'-O-[(ethoxy)diisopropylsilyl]thymidine 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 497070-26-5 5'-O-(4,4'-dimethoxytrityl)thymidyl-(3'->5')-3'-O-[(ethoxy)diisopropylsilyl]thymidine 
• 88819-27-6 C₅₂H₅₁ClN₅O₁₅P 
• 104579-29-5 C₅₅H₅₆N₅O₁₅P 
• 77735-79-6 C₅₂H₅₂N₅O₁₅P 
• 76859-58-0 <(MeO)2Tr>TpTOAc 
• 497070-25-4 C₅₂H₆₆N₅O₁₅PSi 
• 497070-23-2 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(ethoxy)diisopropylsilyl]thymidine 

Downstream Products

• 92127-24-7 C₄₁H₄₅N₄O₁₃PS 

Relevant academic research and scientific papers

Unique participation of unprotected internucleotidic phosphodiester residues on unexpected cleavage reaction of the Si-O bond of the diisopropylsilandiyl group used as a linker for the solid-phase synthesis of 5′-terminal guanylated oligodeoxynucleotides

In connection with the synthesis of guanosine-capped oligodeoxynucleotides on polymer supports, we found an unprecedented Si-O bond cleavage reaction, which occurred when polymer-linked oligodeoxynucleotides having unprotected internucleotidic phosphate groups were allowed to react with the guanosine 5′-phosphorimidazolide derivative 18 in the presence of 4-nitro-6-(trifluoromethyl)-1H-benzotriazol-1-ol (Ntbt-OH) as an effective activator in pyridine. This side reaction was confirmed by the fact that the liquid-phase reaction of DMTrTpT-O-Si(iPr2)OEt 42 with a simpler model compound, methyl phosphorimidazolide 34, in the presence of Ntbt-OH gave DMTrTpT 43. It turned out that the side reaction hardly occurs without unprotected internucleotidic phosphate groups on oligodeoxynucleotides. The detailed study of this side reaction disclosed that Ntbt-OH directly attacks the Si-atom to release oligonucleotides from the resin. It is likely that Ntbt-OH serves as a very strong nucleophile in pyridine, especially to the Si-atom of the linker.

2-MERCAPTOBENZOTHIAZOLE-AN IMPROVED REAGENT FOR THE REMOVAL OF METHYL PHOSPHATE PROTECTING GROUPS FROM OLIGODEOXYNUCLEOTIDE PHOSPHOTRIESTERS.

An equimolar (1.5 M) solution of 2-mercaptobenzothiazole and N,N-diisopropylethylamine in 1-methyl-2-pyrrolidinone efficiently removed the methyl phosphate protecting groups from deoxynucleotide phosphotriesters and yielded synthetic oligomers of high genetic integrity.This odorless reagent can therefore substitute for hazardous thiophenol usually used for this purpose.

USE OF 2-(2-PYRIDYL)ETHYL GROUP AS A NEW PROTECTING GROUP OF INTERNUCLEOTIDIC PHOSPHATES IN OLIGONUCLEOTIDE SYNTHESIS

2-(2-Pyridyl)ethyl group is used as a highly selective protecting group of internucleotidic phosphates that is removable under mild conditions by treatment with CH3I in CH3CN without a side reaction such as N-alkylation.

SPECIFIC REMOVAL OF 5-CHLORO-8-QUINOLYL PROTECTING GROUP OF INTERNUCLEOTIDIC BONDS

5-Chloro-8-quinolyl protecting group of internucleotidic bonds was efficiently removed by treatment with zinc acetate or 2-pyridine-carboxaldehyde oxime at room temperature.On the other hand, alkaline hydrolysis of phosphotriester intermediates with free