136884-17-8

Basic information

• Product Name: 1-[(2R,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]dioxolan-4-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS NO: 136884-17-8
• Molecular Weight: 466.609
• Mol File: 136884-17-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-[(2R,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]dioxolan-4-yl]-5-methyl-1H-pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]dioxolan-4-yl]-5-methyl-1H-pyrimidine-2,4-dione(136884-17-8)
• EPA Substance Registry System: 1-[(2R,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]dioxolan-4-yl]-5-methyl-1H-pyrimidine-2,4-dione(136884-17-8)

Safety Data

• Hazardous Substances Data: 136884-17-8(Hazardous Substances Data)

Upstream product

• 229635-18-1 (2R)-4-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>dioxolane 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 65-71-4 thymin 
• 145365-08-8 (Z)-2,2,11,11-tetramethyl-3,3,10,10-tetraphenyl-4,9-dioxa-3,10-disiladodec-6-ene 
• 145397-22-4 2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]dioxolan-4-one 
• 115869-43-7 (tert-butyldiphenylsilanyloxy)acetaldehyde 
• 136884-15-6 Acetic acid 2-(tert-butyl-diphenyl-silanyloxymethyl)-[1,3]dioxolan-4-yl ester 
• 141119-41-7 (+)-(2R,4R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>dioxolane-4-carboxylic acid methyl ester 
• 136884-14-5 (+)-(2R,4R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>dioxolane-4-carboxylic acid 
• 136884-13-4 (-)-(2R,4R,1'S)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-4-(1,2-dihydroxyethyl)dioxolane 

Downstream Products

• 126652-14-0 (+/-)-dioxolane-T 
• 136982-90-6 (+)-(2R,4S)-1-<2-(hydroxymethyl)-1,3-dioxolan-4-yl>thymine 

Relevant articles and documents

Asymmetric Synthesis of 1,3-Dioxolane-Pyrimidine Nucleosides and Their Anti-HIV Activity

In order to study the structure-activity relationships of dioxolane nucleosides as potential anti-HIV agents, various enantiomerically pure dioxolane-pyrimidine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear cells.The enantiomerically pure key intermediate 8 has been synthesized in nine steps from 1,6-anhydro-D-mannose (1), which was condensed with 5-substituted pyrimidines to obtain various dioxolane-pyrimidine nucleosides.Upon evaluation of these compounds, cytosine derivative 19 was found to exhibit the most potent anti-HIV agent although it is the most toxic.The order of anti-HIV potency was as follows: cytosine (β-isomer) > thymine > cytosine (α-isomer) > 5-chlorouracil > 5-bromouracil > 5-fluorouracil derivatives.Uracil, 5-methylcytosine, and 5-iodouracil derivatives were found to be inactive.Interestingly, α-isomer 20 showed good anti-HIV activity without cytotoxicity.As expected, other α-isomers did not exhibit any significant antiviral activity. (-)-Dioxolane-T was 5-fold less effective against AZT-resistant virus than AZT-sensitive virus.

Asymmetric synthesis of enantiomerically pure (-)-(1'R,4'R)-dioxolane-thymine and its anti-HIV activity

An asymmetric synthesis leading to the enantiomerically pure dioxolane-T has been achieved and its crystal structure has been determined and compared to the previously reported racemate. (-)-(1'R,4'R)-dioxolane-T was found to have potent and selective ant