Bis[3-(triethoxysilyl)propyl]tetrasulfide: The first liquid sulfur-transferring agent useful for conversion of nucleoside phosphites to the phosphorothioates

Tetrahedron

Volumn 61, Issue 4, 2005, Pages 965-970

  Hyodo, Mamoru ^a   Sato, Yumi ^a   Yamashita, Satoko ^a   Hattori, Akira ^a   Kambe, Eri ^a   Kataoka, Masanori ^a   Hayakawa, Yoshihiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Nucleotides; Sulfur compounds; Thiophosphates

Indexed keywords

BIS[3 (TRIETHOXYSILYL)PROPYL]TETRASULFIDE; DNA; NUCLEOSIDE DERIVATIVE; PHOSPHITE; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHOROTHIOIC ACID; RNA; SULFIDE; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; AUTOMATION; LIQUID; PRIORITY JOURNAL; SOLID; SYNTHESIS; TUBE;

EID: 11144294734     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.11.003     Document Type: Article

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35. N-Methyl-2-pyrrolidone and HMPA are rather expensive, and HMPA is highly toxic. tert-Butyl alcohol, the melting point of which is ca. 26°C, runs the risk of freezing in the delivery tubes of the synthesizer.
36. + 529.1574, found 529.1893.
37. In the solid-phase synthesis of a dinucleoside phosphorothioate, 5 min of sulfurization suffices to obtain a high yield of the product. In contrast, for the synthesis of this size of oligomers, i.e. dimers, more time (at least 10 min) is required for sulfurization in order to obtain a satisfactory yield of the target product.
38. According to recent catalogs, the respective prices of TEST and the Beaucage reagent are as follows: TEST costs $280/mol (Gelest), $400/mol (Shin-etsu), $2,500/mol (Fulka), and the Beaucage reagent costs $26,800/mol (Aldrich).
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