3868-27-7

Upstream product

• 121-44-8 triethylamine 
• 160056-33-7 Phenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate 
• 185738-33-4 2'-Deoxy-6-O-(2,5-dichlorophenyl)-5'-O-(4,4'-dimethoxytrityl)-2-N-isobutyrylguanosine 
• 5381-99-7 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 50571-26-1 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 

Downstream Products

• 116631-73-3 C₆₂H₆₃N₄O₁₅P 
• 130767-62-3 C₅₄H₆₂N₇O₁₂PSi 
• 130767-62-3 (R_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-H-phosphonate 
• 130767-62-3 (S_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-H-phosphonate 
• 133471-17-7 (R_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate 
• 133471-17-7 (S_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate 
• 169515-32-6 C₄₆H₅₁N₄O₁₅P 
• 135704-44-8 C₃₆H₄₁N₂O₁₀P 
• 182245-71-2 C₃₇H₄₉N₂O₉PSi₂ 
• 170638-52-5 5'-O-(dimethoxytrityl)thymidin-3'-yl (trimethylsilyl)-H-phosphonate 
• 114797-74-9 C₃₆H₃₆N₃O₉P 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 260262-61-1 4-Nitrophenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate 
• 157793-52-7 p-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphonate 

Relevant academic research and scientific papers

Sulfurization of dinucleoside phosphite triesters with chiral disulfides

Sixteen chiral analogues of phenylacetyl disulfide (PADS) and 5-methyl-3H-1,2,4-dithiazol-3-one (MEDITH) were used to sulfurize five dithymidine phosphite triesters, each incorporating a β-cyanoethoxy or siloxy group. Each mixture of SP:RP phosphite triester diastereomers was combined with approximately one fourth of an equivalent of each of the sulfurizing reagents, and the RPS:SPS diastereomer ratios of the resulting phosphite sulfides or phosphorothioates were determined by reverse-phase HPLC. Diastereoselectivities and corresponding diastereomeric excess (de) values were calculated by correcting for the starting triester diastereomer ratios. The highest de values for RPS and SPS phosphorothioates were 14.7% and 7.9%, respectively, both using MEDITH analogues. Copyright Taylor and Francis Group, LLC.

Synthesis of AZT/d4T boranophosphates as anti-HIV prodrug candidates

AZT/d4T phosphonates were synthesized by sequential condensation of AZT/ d4T with the corresponding alcohols or 5′-DMT-thymidine in the presence of pivaloyl chloride. Sequential silylation, boronation, and hydrolysis in ammonium hydroxide of these phosphonates led to anti-HIV prodrug candidates AZT/d4T boranophosphates.

Synthesis and resolution of dinucleotide(TpAZT) phosphoramidates

Dinucleotide (TpAZT) phosphoramidates were synthesized through Atherton-Todd reaction of dinucleoside H-phosphonates and amino acid methyl esters, and their diastereomers (Rp and Spu) were separated by crystallization. It was showed that the cheap methyl esters of natural alanine and phenylalanine could act as new chiral auxiliaries for large-scale synthesis of dinucleotide analogs.

The H-phosphonate approach to the synthesis of oligonucleotides and their phosphorothioate analogues in solution

A new approach to the synthesis of oligonucleotides and oligonucleotide phosphorothioates in solution is described; it is based on H-phosphonate coupling [with bis(2-chlorophenyl) phosphorochloridate 22 as the coupling agent] at -40 deg C, followed by in situ sulfur transfer involving either 2-(4-chlorophenylsulfanyl)isoindole-1,3(2H)-dione 23a or 4-[(2-cyanoethyl)sulfanyl]morpholine-3,5-dione 26. The yields of the coupling and sulfur transfer reactions are virtually quantitative and, following unblocking by previously reported procedures, very pure products (d[ApC], d[TpGpApC], d[TpGp(s)ApC], d[Gp(s)A] and d[Cp(s)Tp(s)Gp(s)A]) are obtained.

Use of ammonium aryl H-phosphonates in the preparation of nucleoside H-phosphonate building blocks

Ammonium 4-methylphenyl H-phosphonate 4c was used in the conversion of 5'-0-(dimethoxy-trityl)-2'-deoxynucleoside derivatives 6 into the corresponding 3'-H-phosphonates 2, which were isolated in a high state of purity and in high yield.

A Convenient Synthesis of Nucleoside 3'-H-Phosphonate Monoesters Using Triphosgene

A practical method for the preparation of deoxyribonucleoside and ribonucleoside 3'-H-phosphonate monoesters via triphosgene-mediated coupling of nucleosides to phosphonic acid is described.

A convenient and efficient method for the synthesis of nucleoside H-phosphonates using a novel phosphonylating agent

In the present paper we descibe the preparation of a novel crystalline phosphonylating agent 9-fluorenemethyl phosphonic acid 2 and a convenient and efficient method for the synthesis of nucleoside H-phosphonates 5.

Studies on aryl H-phosphonates. I. An efficient method for the preparation of deoxyribo- and ribonucleoside 3'-H-phosphonate monoesters by transesterification of diphenyl H-phosphonate

A convenient method for the preparation of deoxyribonucleoside and ribonucleoside 3'-H-phosphonate monoesters via transesterification of diphenyl H-phosphonate with suitable protected nucleosides in pyridine is described.