39059-59-1Relevant academic research and scientific papers
Bisphosphonate prodrugs: Synthesis of new aromatic and aliphatic 1-hydroxy-1,1-bisphosphonate partial esters
Monteil, Maelle,Guenin, Erwann,Migianu, Evelyne,Lutomski, Didier,Lecouvey, Marc
, p. 7528 - 7537 (2007/10/03)
Methods for the preparation of various 1-hydroxy-1,1-bisphosphonate partial esters were developed. They were obtained from (alkyl or phenyl) bis(trimethylsilyl) phosphite and aromatic or aliphatic acid chlorides, followed by methanolysis.
Application of bromotrimethylsilane and trialkyl phosphites for convenient and effective synthesis of aminophosphonic acids and corresponding monoalkyl and dialkyl esters
Boduszek
, p. 663 - 672 (2007/10/03)
Application of bromotrimethylsilane (Br-TMS) in a mixture with trialkyl phosphite for synthesis of various aminophosphonic acids and esters was investigated. It was found, that appropriate mixtures of Br-TMS and trimethyl phosphite or triethyl phosphite were effective reagents for phosphorylation of various aldimines, obtained from aromatic and heteroaromatic aldehydes. Products of these reactions were corresponding aminophosphonic acids, or corresponding dialkyl or monoalkyl esters, respectively.
Nucleoside H-phosphonates. 18. Synthesis of unprotected nucleoside 5'- H-phosphonates and nucleoside 5'-H-phosphonothioates and their conversion into the 5'-phosphorothioate and 5'-phosphorodithioate monoesters
Jankowska, Jadwiga,Sobkowska, Anna,Cieslak, Jacek,Sobkowski, Michal,Kraszewski, Adam,Stawinski, Jacek,Shugar, David
, p. 8150 - 8156 (2007/10/03)
A simple and efficient protocol for the preparation of unprotected nucleoside 5'-H-phosphonates and nucleoside 5'-H-phosphonothioates via a one- step deprotection of suitable precursors with methylamine has been developed. The synthetic utility of the unprotected nucleotide derivatives was demonstrated by converting them under mild conditions to the corresponding nucleoside 5'-phosphorothioate and nucleoside 5'-phosphorodithioate monoesters. Factors affecting oxidation of H-phosphonate, H-phosphonothioate, and phosphite derivatives with elemental sulfur are also discussed.
A convenient method for phosphorylation involving a facile oxidation of H-Phosphonate monoesters via bis(trimethylsilyl) phosphites
Wada, Takeshi,Mochizuki, Akira,Sato, Yuichi,Sekine, Mitsuo
, p. 7123 - 7126 (2007/10/03)
A new convenient route to phosphate monoesters from alcohols has been developed. H-Phosphonate monoesters, which are readily accessible by phosphonylation of the parent alcohols, were oxidized with t-BuOOH or N- sulfonyloxaziridines under anhydrous conditions via the corresponding bis(trimethylsilyl) phosphites. N,O-Bis(trimethylsilyl)benzamide (BSB) and (camphorsulfonyl)oxaziridine (CSO) were found to be highly effective for silylation of H-phosphonates arid oxidation of silyl phosphites, respectively.
Stereochemistry of the Phosphate-Phosphonate Rearrangement
Hammerschmidt, Friedrich,Voellenkle, Horst
, p. 2053 - 2064 (2007/10/02)
The enantiomerically pure 1-phenylethanols (R)-(+)-5 and (S)-(-)-5 were transformed into the diethyl phpsphates (R)-(+)-6 and (S)-(-)-6, which were subjected a phosphate-phosphonate rearrangement to give the 1-hydroxyphosphonates (-)-7 and (+)-7, respecti
Silyl Phosphites. 15. Reactions of Silyl Phosphites with α-Halo Carbonyl Compounds. Elucidation of the Mechanism of the Perkow Reaction and Related Reactions with Confirmed Experiments
Sekine, Mitsuo,Okimoto, Kiyomi,Yamada, Khoji,Hata, Tsujiaki
, p. 2097 - 2107 (2007/10/02)
The reactions of silyl phosphites, i.e., tris(trimethylsilyl)phosphite (1), diethyl trimethylsilyl phosphite (11), and bis(trimethylsilyl) ethyl phosphite (12), with a variety of α-halo carbonyl compounds gave the 1:1 carbonyl addition products (6, 13, and 14), enol phosphates (5 and 26), and/or 2-oxophosphonates (4 and 25).Substituents on the phosphites and the α-halo carbonyl compounds have influenced the product ratios.The results of these reactions strongly suggest that the Perkow reaction proceeds via an initial attack of phosphite on the carbonyl carbon of the α-halo carbonyl compound.Treatment of bis(trimethylsilyl) 1--2-halo phosphonates (6) with sodium methoxide in methanol followed by retrimethylsilylation gave bis(trimethylsilyl) 1,2-epoxy phosphonates (17), bis(trimethylsilyl) 2-oxo phosphonates (4), and bis(trimethylsilyl) methyl phosphate (21).On the other hand, diethyl 1-hydroxy-2-halo phosphonates (22) were converted by treatment with different bases to 1,2-epoxy phosphonates (23) predominantly in good yields.When some of tri-n-butyltin alkoxides were used as bases, enol phosphates (26) were obtained selectively.Several bis(trimethylsilyl) esters obtained in the above reactions were successfully converted to the corresponding monoanilinium salts in high yields by treatment with aniline-containing alcohols.
