3868-27-7

Basic information

• Product Name: dmt-thymidine H-phosphonate*triethylammonium
• CAS NO: 3868-27-7
• Molecular Formula: C₆H₁₅N*C₃₁H₃₃N₂O₉P
• Molecular Weight: 709.77
• Mol File: 3868-27-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: dmt-thymidine H-phosphonate*triethylammonium(CAS DataBase Reference)
• NIST Chemistry Reference: dmt-thymidine H-phosphonate*triethylammonium(3868-27-7)
• EPA Substance Registry System: dmt-thymidine H-phosphonate*triethylammonium(3868-27-7)

Safety Data

• Hazardous Substances Data: 3868-27-7(Hazardous Substances Data)

Upstream product

• 121-44-8 triethylamine 
• 160056-33-7 Phenyl 5'-O-dimethoxytritylthymidin-3'-yl phosphonate 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 50571-26-1 5'-O-dimethoxytritylthymidine 3'-H-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 

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 articles and documents

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 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.

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.