1053649-58-3

Basic information

• Product Name: Benzoic acid (3aR,5R,6R,6aR)-5-iodoethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS NO: 1053649-58-3
• Molecular Weight: 414.197
• Mol File: 1053649-58-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid (3aR,5R,6R,6aR)-5-iodoethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (3aR,5R,6R,6aR)-5-iodoethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester(1053649-58-3)
• EPA Substance Registry System: Benzoic acid (3aR,5R,6R,6aR)-5-iodoethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester(1053649-58-3)

Safety Data

• Hazardous Substances Data: 1053649-58-3(Hazardous Substances Data)

Upstream product

• 214038-36-5 (3aR,5R,6R,6aR)-5-(2,2-Dibromo-vinyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 214038-37-6 5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hex-5-ynofuranose 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 66926-91-8 Benzoic acid (3aR,5R,6R,6aR)-5-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Relevant articles and documents

Inactivation of S-adenosyl-L-homocysteine hydrolase and antiviral activity with 5',5',6',6'-tetradehydro-6'-deoxy-6'-halohomoadenosine analogues (4'-haloacetylene analogues derived from adenosine)

Treatment of a protected 9-(5,6-dideoxy-β-D-ribo-hex-5- ynofuranosyl)adenine derivative with silver nitrate and N-iodosuccinimide (NIS) and deprotection gave the 6'-iodo acetylenic nucleoside analogue 3c. Halogenation of 3-O-benzoyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hex- 5-enofuranose gave 6-halo acetylenic sugars that were converted to anomeric 1,2-di-O-acetyl derivatives and coupled with 6-N-benzoyladenine. These intermediates were deprotected to give the 6'-chloro 3a, 6'-bromo 3b, and 6'- iodo 3c acetylenic nucleoside analogues. Iodo compound 3c appears to inactivate S-adenosyl-L-homocysteine hydrolase by a type I ('cofactor depletion') mechanism since complete reduction of enzyme-bound NAD+ to NADH was observed and no release of adenine or iodide ion was detected. In contrast, incubation of the enzyme with the chloro 3a or bromo 3b analogues resulted in release of Cl- or Br- and Ade, as well as partial reduction of E-NAD+ to E-NADH. Compounds 3a, 3b, and 3c were inhibitory to replication of vaccinia virus, vesicular stomatitis virus, parainfluenza-3 virus, and reovirus-1 (3a 3b 3c, in order of increasing activity). The antiviral effects appear to correlate with type I mechanism-based inhibition of S- adenosyl-L-homocysteine hydrolase. Mechanistic considerations are discussed.