214900-47-7

Basic information

• Product Name: Methanesulfonic acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methanesulfonyloxy-tetrahydro-furan-3-yl ester
• CAS NO: 214900-47-7
• Molecular Weight: 661.832
• Mol File: 214900-47-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Methanesulfonic acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methanesulfonyloxy-tetrahydro-furan-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methanesulfonyloxy-tetrahydro-furan-3-yl ester(214900-47-7)
• EPA Substance Registry System: Methanesulfonic acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methanesulfonyloxy-tetrahydro-furan-3-yl ester(214900-47-7)

Safety Data

• Hazardous Substances Data: 214900-47-7(Hazardous Substances Data)

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 119898-65-6 (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol 
• 58-61-7 adenosine 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Relevant articles and documents

Nucleic acid related compounds. 105. Synthesis of 2',3'-didehydro- 2',3'-dideoxynucleosides from ribonucleoside cyclic 2',3'-(Sulfates or phosphates) or 2',3'-dimesylates via reductive elimination with sodium naphthalenide

Treatment of purine ribonucleosides with thionyl fluoride resulted in formation of cyclic 2',3'-sulfite esters. Acetylation of the 5'-hydroxy group and Sharpless oxidation (NaIO4/RuCl3) gave the cyclic 2',3'-sulfate ester derivatives. Treatment of 5'-O-silyl-protected ribonucleosides with thionyl chloride followed by oxidation gave an alternative route to the cyclic 2',3'- sulfates. Reductive elimination with sodium naphthalenide (THF/-50 °C) gave the 2',3'-unsaturated nucleosides. Parallel treatment of adenosine cyclic 2',3'-phosphate gave the 2',3'-olefin. The adenine, hypoxanthine, and 2- amino-6-methoxypurine 2',3'-didehydro-2',3'-dideoxynucleosides were prepared efficiently (40-60% overall yields of crystalline, analytically pure products; 3-5 steps, some combined into one-flask procedures) by treatment of 5'-O-protected 2',3'-di-O-mesylribonucleosides with sodium naphthalenide. Reactions were performed at or below ambient temperature with readily available reagents and standard laboratory conditions.