179090-12-1

Basic information

• Product Name: 5'-O-DMT-thymidine 3'-O-(2-thio-1,3,2-oxathiaphospholane)
• Synonyms: 5'-O-DMT-thymidine 3'-O-(2-thio-1,3,2-oxathiaphospholane)
• CAS NO: 179090-12-1
• Molecular Weight: 682.755
• Mol File: 179090-12-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5'-O-DMT-thymidine 3'-O-(2-thio-1,3,2-oxathiaphospholane)(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-DMT-thymidine 3'-O-(2-thio-1,3,2-oxathiaphospholane)(179090-12-1)
• EPA Substance Registry System: 5'-O-DMT-thymidine 3'-O-(2-thio-1,3,2-oxathiaphospholane)(179090-12-1)

Safety Data

• Hazardous Substances Data: 179090-12-1(Hazardous Substances Data)

Upstream product

• 186500-26-5 1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-([1,3,2]oxathiaphospholan-2-yloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 182370-37-2 Thiophosphorofluoridic acid O-[(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 

Relevant articles and documents

Diastereomers of nucleoside 3'-O-(2-thio-1,3,2-oxathia(selena)phospholanes): Building blocks for stereocontrolled synthesis of oligo(nucleoside phosphorothioate)s

Diastereomerically pure 5'-O-DMT-nucleoside 3'-O-(2-thio-1,3,2-oxathiaphospholanes) (3) and their oxathiaphospholane ring-substituted analogues (20) were used for the synthesis of stereoregular oligo(nucleoside phosphorothioate)s (S-Oligos). The oxathiaphospholane ring-opening condensation requires the presence of strong organic base, preferably DBU. The yield of a single coupling step is ca. 95% and resulting S-Oligos are free of nucleobase- and sugar-phosphorothioate backbone modifications. The diastereomeric purity of products was estimated on the basis of diastereoselective degradation with Nuclease P1 and a mixture of snake venom phosphodiesterase and Serratia marcescens endonuclease. Thermal dissociation studies of heteroduplexes S-Oligos/DNA and S-Oligos/RNA showed that their stability is stereochemistry- and sequence-dependent.