141845-83-2

Basic information

• Product Name: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione
• CAS NO: 141845-83-2
• Molecular Formula: C₂₃H₄₁N₃O₈SSi₂
• Molecular Weight: 575.8229
• Mol File: 141845-83-2.mol
• Article Data: 3

Chemical Properties

• Density: 1.24g/cm³
• Refractive Index: 1.544
• CAS DataBase Reference: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione(141845-83-2)
• EPA Substance Registry System: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione(141845-83-2)

Safety Data

• Hazardous Substances Data: 141845-83-2(Hazardous Substances Data)

Usage

Chemical structure

A complex chemical compound with a pyrimidine-2,4(1H,3H)-dione backbone and multiple functional groups, including an amino group and tert-butyl(dimethyl)silyl groups.

Stereochemistry

The compound has a specific stereochemistry, with the 6R, 8R, and 9R configurations.

Functional groups

The compound contains an amino group, tert-butyl(dimethyl)silyl groups, and a 2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl group.

Biological activity

The compound is a potent inhibitor of a specific enzyme or protein and is used in biological and biochemical research to study the role and function of the target enzyme or protein in various cellular processes.

Applications

The compound has potential applications in scientific research and organic synthesis due to its complex structure and functional groups.

Protecting group

The presence of tert-butyl(dimethyl)silyl groups in the chemical structure suggests that it may also have applications as a protecting group for sensitive functional groups in chemical reactions.

Solubility

The compound's solubility properties are not specified in the provided material, but it is likely to be soluble in organic solvents due to the presence of the tert-butyl and dimethyl groups.

Stability

The compound's stability properties are not specified in the provided material, but the presence of the tert-butyl(dimethyl)silyl groups may contribute to its stability in certain chemical reactions.

Synthesis

The synthesis of this complex compound likely involves multiple steps and the use of various protecting groups and reaction conditions to achieve the desired stereochemistry and functional groups.

Purity

The purity of the compound is not specified in the provided material, but it is important to consider when using the compound in research or synthesis to ensure accurate results.

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 141684-50-6 1-((5S,6R,8R,9R)-4-Amino-9-hydroxy-6-hydroxymethyl-2,2-dioxo-1,7-dioxa-2λ⁶-thia-spiro[4.4]non-3-en-8-yl)-1H-pyrimidine-2,4-dione 
• 142102-72-5 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl)uracil 
• 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 
• 90813-54-0 2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine 
• 141706-85-6 1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl>uracil 
• 6698-46-0 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 

Downstream Products

• 142102-78-1 <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>cytosine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) 
• 142102-83-8 <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-3-N-allyluracil>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) 

Relevant articles and documents

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

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.