126999-87-9

Upstream product

• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 4712-55-4 diphenyl hydrogen phosphite 
• 121-44-8 triethylamine 
• 3868-27-7 triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 

Downstream Products

• 173204-31-4 5'-O-dimethoxytritylthymidin-3'-yl trimethylsilyl H-phosphonothioate 
• 351341-22-5 5'-O-(dimethoxytrityl)thymidin-3'-yl 3'-O-(dimethoxytrityl)thymidin-5'-yl H-phosphonothioate 
• 351341-22-5 5'-O-(dimethoxytrityl)thymidin-3'-yl 3'-O-(dimethoxytrityl)thymidin-5'-yl H-phosphonothioate 
• 157793-51-6 3'-O-(4,4'-dimethoxytrityl)thymidin-5'-yl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl ethyl phosphonate 
• 650601-44-8 O-(5'-dimethoxytrityl-2'-deoxythymidin-3'-yl)-O-(3'-azido-2'-deoxythymidin-5'-yl) H-thiophosphonate 
• 182245-84-7 C₃₆H₃₆N₃O₈PS 
• 124667-73-8 C₅₃H₅₇N₄O₁₄PS 
• 1035457-84-1 C₆H₁₅N*C₃₂H₃₅N₂O₉PS 
• 1035457-89-6 C₆H₁₅N*C₃₅H₄₁N₂O₉PS 
• 650601-57-3 O-(5'-dimethoxytrityl-2'-deoxythymidin-3'-yl)-O-(2',3'-dideoxythymidin-5'-yl) H-thiophosphonate 
• 135257-77-1 C₄₈H₄₉N₄O₁₃PS 

Relevant academic research and scientific papers

Silylation-mediated transesterification of O-phenyl H-phosphonothioates - A new entry to nucleoside H-phosphonothioate monoesters

O-Phenyl H-phosphonothioate undergoes a facile transesterification with suitably protected nucleosides upon in situ silylation with tert- butyldiphenylsilyl chloride in pyridine/toluene to produce the corresponding 3′-H-phosphonothioates in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis of dinucleotide thiophosphoramidates as anti-HIV new prodrugs

Sequential transesterification of diphenyl phosphite with 5′-O-(4,4′-dimethoxytrityl)thymidine (1) and hydrogen sulfide gave O-[5′-O-(4,4′-dimethoxytrityl)thymidine-3′-yl] H-thiophosphonate (2), and subsequent condensation of 2 with AZT or d4T in the presence of diphenyl chlorophosphoate provided the dinucleotide H-thiophosphonates 3 or 3′. The Antherton-Todd reaction of 3 or 3′ with L-amino acid methyl ester in a solution of CCl4-Et 3N-H2O-MeCN gave the dinuleotide thiophosphoramidates 4 or 4′, and removal of the dimethoxytrityl protecting group in formic acid yielded the target products AZT/d4T thiophosphoramidates 5 and 5′.

Aryl H-Phosphonates. 12. Synthetic and 31P NMR Studies on the Preparation of Nucleoside H-Phosphonothioate and Nucleoside H-Phosphonodithioate Monoesters

Transformation of nucleoside H-phosphonate monoesters into the corresponding H-phosphonothioate and H-phosphonodithioate derivatives and possible side-reactions that may accompany this process were studied using 31P NMR spectroscopy. These provided new insight into a possible mechanism involved in this transformation and constituted the basis for development of efficient methods for the preparation of nucleoside H-phosphonothioate and nucleoside H-phosphonodithioate monoesters using readily available H-phosphonate monoesters as starting materials.

NUCLEOSIDE H-PHOSPHONATES. X. STUDIES ON NUCLEOSIDE HYDROGENPHOSPHONOTHIOATE DIESTER SYNTHESIS

Synthesis and chemical properties of nucleoside H-phosphonothioates are discussed in the context of possible application of these compounds as intermediates in the synthesis of oligonucleotide analogues.