175020-66-3

Basic information

• Product Name: 2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone
• Synonyms: 2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone
• CAS NO: 175020-66-3
• Molecular Weight: 608.925
• Mol File: 175020-66-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone(175020-66-3)
• EPA Substance Registry System: 2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone(175020-66-3)

Safety Data

• Hazardous Substances Data: 175020-66-3(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 34371-14-7 2-deoxy-D-ribonolactone 

Downstream Products

• 105930-84-5 tert-butyl(((2R,3S)-3-((tert-butyldiphenylsilyl)oxy)-2,3-dihydrofuran-2-yl)methoxy)diphenylsilane 
• 130277-32-6 ((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2,3-dihydrofuran-2-yl)methanol 
• 940285-39-2 1-O-acetyl-3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-D-ribofuranose 
• 940285-57-4 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-E-vinyl]-5-methyl-thiazol-2-one 
• 940285-56-3 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-5-methyl-thiazol-2-one 
• 940285-55-2 4-[2-(3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl)-Z-vinyl]-N-(4-methoxybenzyl)-5-methyl-thiazol-2-one 
• 940285-45-0 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl carbaldehyde 
• 940285-42-7 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-β-D-ribofuranosyl cyanide 
• 940285-41-6 3,5-bis-O-(t-butyldiphenylsilyl)-2-deoxy-α-D-ribofuranosyl cyanide 

Relevant articles and documents

A facile, multigram synthesis of ribofuranoid glycals

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Discovery of a Series of 2′-α-Fluoro,2′-β-bromo-ribonucleosides and Their Phosphoramidate Prodrugs as Potent Pan-Genotypic Inhibitors of Hepatitis C Virus

Hepatitis C virus (HCV) nucleoside inhibitors display pan-genotypic activity, a high barrier to the selection of resistant virus, and are some of the most potent direct-acting agents with durable sustained virologic response in humans. Herein, we report, the discovery of β-d-2′-Br,2′-F-uridine phosphoramidate diastereomers 27 and 28, as nontoxic pan-genotypic anti-HCV agents. Extensive profiling of these two phosphorous diastereomers was performed to select one for in-depth preclinical profiling. The 5′-triphosphate formed from these phosphoramidates selectively inhibited HCV NS5B polymerase with no inhibition of human polymerases and cellular mitochondrial RNA polymerase up to 100 μM. Both are nontoxic by a variety of measures and display good stability in human blood and favorable metabolism in human intestinal microsomes and liver microsomes. Ultimately, a preliminary oral pharmacokinetics study in male beagles showed that 28 is superior to 27 and is an attractive candidate for further studies to establish its potential value as a new clinical anti-HCV agent.

Direct and facile syntheses of heterocyclic vinyl-C-nucleosides for recognition of inverted base pairs by DNA triple helix formation: First report by direct Wittig route

(Chemical Equation Presented) The ability to recognize specific gene sequences canonically would allow precise means for genetic intervention. However, specific recognition of two of the four possible base pairs by triplex-forming oligonucleotides (TFO) as X·T-A and Y·C-G within a triplex currently remains elusive. A series of C1-vinyl nucleosides have been proposed, and their stability and specificity have been evaluated extensively by molecular dynamics simulation. Because most C-nucleoside syntheses extend through direct substitution at the C1-position, a more convenient strategy for their syntheses via a direct Wittig coupling is presented here.