267667-52-7

Basic information

• Product Name: (2R,5S)- and (2R,5R)-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3,5(2H,4H)-dione
• Synonyms: (2R,5S)- and (2R,5R)-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3,5(2H,4H)-dione
• CAS NO: 267667-52-7
• Molecular Weight: 469.637
• Mol File: 267667-52-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,5S)- and (2R,5R)-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3,5(2H,4H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)- and (2R,5R)-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3,5(2H,4H)-dione(267667-52-7)
• EPA Substance Registry System: (2R,5S)- and (2R,5R)-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3,5(2H,4H)-dione(267667-52-7)

Safety Data

• Hazardous Substances Data: 267667-52-7(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 134678-17-4 lamivudine 
• 145985-97-3 (2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine 
• 17331-61-2 3,5-bis(trimethylsilyloxy)-1,2,4-triazine 

Downstream Products

• 267667-55-0 (2R,5R)-5-amino-2-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3(2H)-one 
• 267667-54-9 (2R,5S)-5-amino-2-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3(2H)-one 

Relevant articles and documents

Synthesis and biological evaluation of 1,3-oxathiolane 5-azapyrimidine, 6-azapyrimidine, and fluorosubstituted 3-deazapyrimidine nucleosides

(2R,5S)-5-Amino-2-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2,4- triazine-3(2H)-one (8) and (2R,5R)-5-amino-2-[2-(hydroxymethyl)-1,3- oxathiolan-5-yl]-1,2,4-triazine-3(2H)-one (9) have been synthesized via a multi-step procedure from 6-azauridine. (2R,5S)-4-Amino-1-[2-(hydroxymethyl)- 1, 3-oxathiolan-5-yl]-1,3,5-triazine-2(1H)-one (11) and (2R,5R)-4-amino-1-[2- (hydroxymethyl)-1,3-oxathiolan-5-yl]-1,3,5-triazine-2(1H)-one (12), and the fluorosubstituted 3-deazanucleosides (19-24) have been synthesized by the transglycosylation of (2R,5S)-1-{2-[[(tert-butyldiphenylsilyl) oxy]methyl]- 1,3-oxathiolan-5-yl}cytosine (2) with silylated 5-azacytosine and the corresponding silylated fluorosubstituted 3-deazacytosines, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst in anhydrous dichloroethane, followed by deprotection of the blocking groups. These compounds were tested in vitro for cytotoxicity against L1210, B16F10, and CCRF-CEM tumor cell lines and for antiviral activity against HIV-1 and HBV.