141781-17-1

Basic information

• Product Name: (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine
• Synonyms: (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine;TSAO-T;TSAO;1-[(5R,6R,8R,9R)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dioxo-1,7-dioxa-2$l^{6}-thiaspiro[4.4]non-3-en-8-yl]-5-methylpyrimidine-2,4-dione
• CAS NO: 141781-17-1
• Molecular Formula: C₂₄H₄₃N₃O₈SSi₂
• Molecular Weight: 589.855
• Mol File: 141781-17-1.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.22g/cm³
• CAS DataBase Reference: (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine(141781-17-1)
• EPA Substance Registry System: (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine(141781-17-1)

Safety Data

• Hazardous Substances Data: 141781-17-1(Hazardous Substances Data)

Usage

Uses

Used in Nucleic Acid Research:
(2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine is used as a research tool for studying the interactions between nucleic acids and other molecules. Its unique structure allows for the investigation of various biological processes and mechanisms.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine may be utilized as a potential therapeutic agent. Its complex structure and specific modifications could offer new avenues for the development of treatments targeting various diseases and conditions.

Upstream product

• 142102-74-7 <1-(2'-O-acetyl-5'-O-benzoyl-β-D-ribofuranosyl)thymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) 
• 142102-71-4 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl)thymine 
• 151215-43-9 1,2-di-O-acetyl-5-O-benzoyl-3-C-cyano-3-O-mesyl-D-ribofuranose 
• 142131-02-0 5-O-benzoyl-3-C-cyano-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose 
• 250588-64-8 Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 
• 117174-40-0 (2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile 
• 6698-46-0 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 
• 117174-33-1 1-<2,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine 
• 82101-74-4 methyl (E)-3-(tributylstannyl)acrylate 
• 307953-57-7 [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine]-3'-spiro-5''-(4''-amino-3''-iodo-1'',2''-oxathiole-2'',2''-dioxide) 
• 141684-44-8 1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl>thymine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 141781-18-2 <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 

Downstream Products

• 141781-18-2 <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 
• 141684-47-1 <1-<2'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 
• 142102-77-0 TSAO-m5C 
• 1338582-75-4 [1-[2',5'-bis-O-tert-butyldimethylsilyl-β-D-ribofuranosyl]-3-N-benzoylthymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide) 
• 1338582-85-6 [1-[2',5'-bis-O-tert-butyldimethylsilyl-β-D-ribofuranosyl]-3-N-(benzyloxyglutaryl)thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide) 
• 1338582-86-7 [1-[2',5'-bis-O-tert-butyldimethylsilyl-β-D-ribofuranosyl]-3-N-(N-benzylaminoglutaryl)thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide) 
• 142102-81-6 <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-3-N-allylthymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) 
• 142102-80-5 <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-3-N-ethylthymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) 
• 142102-79-2 TSAO-m3T 
• 141684-48-2 <1-<5'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 
• 141684-49-3 <1-<5'-O-(tert-butyldimethylsilyl)-2'-deoxy-β-D-erythro-pentofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 

Relevant articles and documents

Novel tsao derivatives modified at positions 3″ and 4″ of the spiro moiety

We have explored the introduction of different functional groups at positions 3″ and 4″ of the spiro moiety of TS AO-T. Alkylation of this spiro moiety afforded mixtures of N and/or C-alkylated derivatives, while acylation occurs, exclusively, on the amino group. Position 3" has been selectively functionalized by halogenation followed by Stille-cross coupling reaction with organostannanes under a variety of experimental conditions. Copyright

An efficient synthesis of 3'-spiro sultone nucleosides functionalized on the sultone moiety via Pd-catalyzed cross-coupling reaction

We describe the first efficient application of the Stille coupling reaction on iodo 3'-spiro sultone nucleosides. The yield and rate of the reaction are significantly affected by the addition of copper iodide as cocatalyst, AsPh3 as ligand and organostannane stoichiometry. Using this technology a number of alkenyl-, phenyl- and allyl-substituted 3'-spiro sultone nucleosides were produced.

TSAO derivatives: Highly specific inhibitors of human immunodeficiency virus type-1 (HIV-1) replication

TSAO derivatives represent a unique class of nucleosides that are specifically targeted at HIV-1 RT. This overview is focussed on the chemical synthesis, the conformational studies, the antiviral and metabolic properties of TSAO derivatives, as well as th

TSAO analogues. Stereospecific synthesis and anti-HIV-1 activity of 1- [2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3'-spiro-5''-(4''- amino-1'',2''-oxathiole 2'',2''-dioxide) pyrimidine and pyrimidine-modified nucleosides

Several analogues of a new lead for anti-HIV-1 agents [1-[2',5'-bis-O- (tert-butyldimethylsilyl)-β-D-ribofuranosyl]-thymine]-3'-spiro-5''-(4''- amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) modified at positions N-3, O- 4 and C-5 of the thymine moiety,

Synthesis of {1-[2',5'-bis-O-(t-butyldimethylsilyl)-β-D-xylo- and β-D-ribofuranosyl]Thymine}-3'-spiro-5''-{4''-amino-1'',2''-oxathiol e-2'',2''-dioxide} (TSAO). A novel type of specific anti-HIV agents

Reaction of O-mesylcyanohydrins of furanos-3'-ulosyl thymine with bases afforded β-D-xylo- and ribo-3'-substituted nucleosides. 2'-Deoxygenation of the selectively 5'-O-protected nucleoside gave the ribofuranosyl derivative of thymidine.

3'-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: Synthesis and antiviral activity of [2',5'-bis-O-(tert- butyldimethylsilyl)-β-D-xylo- and -ribofuranose]-3'-spiro-5''-[4''-amino- 1'',2''-oxathiole 2'',2''-dioxide] (TSAO) pyrimidine nucleosides

A series of 3'-spiro nucleosides have been synthesized and evaluated as anti-HIV-1 agents. Reaction of O-mesyl-cyanohydrins of furanos-3'-ulosyl nucleosides with base afforded [1,[2',5'-bis-O-(tert-butyldimethylsilyl)-β- D-xylo- and -ribofuranosyl]]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole 2'',2''-dioxide] derivatives of thymine, uracil and 4-N-acetylcytosine 11 and 12. Desilylation of 11 and 12 gave the full deprotected 3'-spiro xylo- and ribofuranosyl nucleosides 13 and 14 or the partially 5'-O-deprotected-3'- spiro β-D-xylo- and -ribo-nucleosides 15 and 16, or 2'-O-deprotected-3'- spiro β-D-ribo-nucleoside 17. 2'-Deoxygenation of 17 afforded 2'-deoxy-3'- spiro β-D-erythro-pentofuranosyl derivative 18. These 3'-spiro derivatives were evaluated for their anti-HIV-1 activity. All 3'-spiro nucleosides having a xylo configuration did not show any anti-HIV-1 activity. 3'-Spiro ribo- nucleosides with none or only one silyl group at C-2' or C-5' or the 2'-deoxy derivative were also inactive at subtoxic concentrations. However, 3'-spiro ribo-nucleosides having two silyl groups at C-2' and C-5' were potent and selective inhibitors of HIV-1. None of the nucleoside analogues that showed anti-HIV-1 activity proved inhibitory to the replication of HIV-2 or SIV.