141684-51-7

Basic information

• Product Name: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione
• CAS NO: 141684-51-7
• Molecular Formula: C₁₇H₂₇N₃O₈SSi
• Molecular Weight: 461.5621
• Mol File: 141684-51-7.mol
• Article Data: 1

Chemical Properties

• Density: 1.42g/cm³
• Refractive Index: 1.595
• CAS DataBase Reference: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-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-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione(141684-51-7)
• EPA Substance Registry System: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione(141684-51-7)

Safety Data

• Hazardous Substances Data: 141684-51-7(Hazardous Substances Data)

Usage

General Description

The chemical "1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione" is a complex organic molecule with a pyrimidine-2,4(1H,3H)-dione core. It contains a 4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl side chain, with a specific configuration of stereochemistry denoted by the (6R,8R,9R) prefix. 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione may have potential applications in pharmaceutical and chemical research due to its unique structure and functional groups.

Upstream product

• 141706-84-5 1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-xylofuranosyl>uracil 
• 90813-54-0 2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine 
• 141706-86-7 <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-xylofuranosyl>uracil>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> 

Relevant articles and documents

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.