137058-84-5

Basic information

• Product Name: 6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-iodo-2-methylene-β-D-erythro-pentofuranosyl)adenine
• Synonyms: 6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-iodo-2-methylene-β-D-erythro-pentofuranosyl)adenine
• CAS NO: 137058-84-5
• Molecular Weight: 695.632
• Mol File: 137058-84-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-iodo-2-methylene-β-D-erythro-pentofuranosyl)adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-iodo-2-methylene-β-D-erythro-pentofuranosyl)adenine(137058-84-5)
• EPA Substance Registry System: 6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-iodo-2-methylene-β-D-erythro-pentofuranosyl)adenine(137058-84-5)

Safety Data

• Hazardous Substances Data: 137058-84-5(Hazardous Substances Data)

Upstream product

• 90813-59-5 9-(3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-2-ulosyl)adenine 
• 58-61-7 adenosine 
• 137058-83-4 Toluene-4-sulfonic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methylene-tetrahydro-furan-2-ylmethyl ester 
• 137058-82-3 9-(2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine 
• 137058-78-7 9-(3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)adenine 
• 104409-41-8 2'-deoxy-2'-methyleneadenosine 
• 98-88-4 benzoyl chloride 
• 69504-03-6 3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine 
• 137091-53-3 6-N,N-dibenzoyl-9-(3-O-(tert-butyldimethylsilyl)-2-deoxy-2-methylene-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranosyl)adenine 

Relevant articles and documents

Nucleic Acid Related Compounds. 70. Synthesis of 2'(and 3')-Deoxy-2'(and 3')-methyleneadenosines and Bis(methylene)furan 4',5'-Didehydro-5'-deoxy-2'(and 3')-methyleneadenosines. Inhibitors of S-Adenosyl-L-homocysteine Hydrolase and Ribonucleotide Reductase

Wittig treatment of 3',5'(or 2',5')-bis-O-silyl-2'(or 3')-ketoadenosine derivatives with methylenetriphenylphosphorane and deprotection gave the 2'(or 3')-deoxy-2'(or 3')-methyleneadenosines, respectively.Enzymatic deamination afforded the 2'(or 3')-deoxy-2'(or 3')-methyleneinosines.Treatment of 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-methylene-5'-O-tosyladenosine (14) with sodium 2-methyl-2-butoxide and deprotection gave 9-(3,5-dideoxy-3-methylene-β-D-glycero-pent-4-enofuranosyl)adenine (20).Analogous treatment of a protected 2',5'-dideoxy-5'-iodo-2'-methyleneadenosine derivative gave 9-(2,5-dideoxy-2-methylene-β-D-glycero-pent-4-enofuranosyl)adenine (22).Biochemical aspects of the putative mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase by these compounds are discussed.