2-Trimethylsilylethyl Sulfides in the von Braun Cyanogen Bromide Reaction:  Selective Preparation of Thiocyanates and Application to Nucleoside Chemistry

Mixed 2-(trimethylsilyl)ethyl sulfides were synthesized and used in the von Braun cyanogen bromide reaction for preparing selectively thiocyanates in high yield. We show here that this cleavage reaction is highly selective in methanol in comparison with the reaction of the corresponding non-silyl su...

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Published inJournal of organic chemistry Vol. 67; no. 6; pp. 1898 - 1904
Main Authors Chambert, Stéphane, Thomasson, François, Décout, Jean-Luc
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.03.2002
Amer Chemical Soc
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Abstract Mixed 2-(trimethylsilyl)ethyl sulfides were synthesized and used in the von Braun cyanogen bromide reaction for preparing selectively thiocyanates in high yield. We show here that this cleavage reaction is highly selective in methanol in comparison with the reaction of the corresponding non-silyl sulfide analogues. This reaction was applied to the synthesis of nucleosidic thiocyanates such as the new nucleosides 14 and 18 in the search for mechanism-based inhibitors of ribonucleoside diphosphate reductase and bioactive molecules. The selective cleavage is possible for sulfides bearing hydroxyl functions and aromatic rings. The reactions of cyanogen bromide as cyanating and brominating agent were observed for the first time under the same conditions with the naphthoxyhexyl 2-trimethylsilylethyl sulfide 7, which, treated with cyanogen bromide in dichloromethane, led selectively to the p-bromonaphthoxyhexyl thiocyanate 10 in 89% yield. Another reaction induced by cyanogen bromide was observed in dichloromethane with the 2-(trimethylsilylethyl)thio nucleoside 13, which gives the corresponding symmetrical disulfide 21 in good yield.
AbstractList Mixed 2-(trimethylsilyl)ethyl sulfides were synthesized and used in the von Braun cyanogen bromide reaction for preparing selectively thiocyanates in high yield. We show here that this cleavage reaction is highly selective in methanol in comparison with the reaction of the corresponding non-silyl sulfide analogues. This reaction was applied to the synthesis of nucleosidic thiocyanates such as the new nucleosides 14 and 18 in the search for mechanism-based inhibitors of ribonucleoside diphosphate reductase and bioactive molecules. The selective cleavage is possible for sulfides bearing hydroxyl functions and aromatic rings. The reactions of cyanogen bromide as cyanating and brominating agent were observed for the first time under the same conditions with the naphthoxyhexyl 2-trimethylsilylethyl sulfide 7, which, treated with cyanogen bromide in dichloromethane, led selectively to the p-bromonaphthoxyhexyl thiocyanate 10 in 89% yield. Another reaction induced by cyanogen bromide was observed in dichloromethane with the 2-(trimethylsilylethyl)thio nucleoside 13, which gives the corresponding symmetrical disulfide 21 in good yield.
Author Décout, Jean-Luc
Thomasson, François
Chambert, Stéphane
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Issue 6
Keywords INACTIVATION
ACID RELATED-COMPOUNDS
SELF-ASSEMBLED MONOLAYERS
L-HOMOCYSTEINE HYDROLASE
2-(TRIMETHYLSILYL)ETHYL SULFIDES
ALKYL THIOCYANATES
ANALOGS
MECHANISM-BASED INHIBITORS
DERIVATIVES
S-ADENOSYLHOMOCYSTEINE HYDROLASE
Adenine derivatives
Solvent effect
Organic thiocyanate
Purine nucleoside
Chemoselectivity
Organic silane
Bromine Cyanides
Organic sulfide
Dideoxynucleoside
Thioglycoside
Dichloromethane
Aromatic compound
Chemical synthesis
Pyrimidine nucleoside
Methanol
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SSID ssj0000555
Score 1.8297613
Snippet Mixed 2-(trimethylsilyl)ethyl sulfides were synthesized and used in the von Braun cyanogen bromide reaction for preparing selectively thiocyanates in high...
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SubjectTerms Bromine - chemistry
Carbohydrates. Nucleosides and nucleotides
Catalysis
Chemistry
Chemistry, Organic
Chemistry, Organic - methods
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Exact sciences and technology
Magnetic Resonance Spectroscopy
Methanol - chemistry
Molecular Structure
Nucleosides - chemistry
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Silanes - chemical synthesis
Silanes - chemistry
Sulfides - chemical synthesis
Sulfides - chemistry
Thiocyanates - chemistry
Title 2-Trimethylsilylethyl Sulfides in the von Braun Cyanogen Bromide Reaction:  Selective Preparation of Thiocyanates and Application to Nucleoside Chemistry
URI http://dx.doi.org/10.1021/jo016200q
https://api.istex.fr/ark:/67375/TPS-0NX670XZ-V/fulltext.pdf
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Volume 67
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