249757-27-5

Basic information

• Product Name: 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)purine
• Synonyms: 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)purine
• CAS NO: 249757-27-5
• Molecular Weight: 569.06
• Mol File: 249757-27-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)purine(249757-27-5)
• EPA Substance Registry System: 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)purine(249757-27-5)

Safety Data

• Hazardous Substances Data: 249757-27-5(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 39824-26-5 6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine 

Downstream Products

• 249757-36-6 6-chloro-2-(cyclohexyl)hydroxymethyl-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 
• 249757-37-7 6-chloro-2-(1-hydroxy-1-methyl)ethyl-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 
• 249757-41-3 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-2-(methoxycarbonyl)-8-(triisopropylsilyl)purine 
• 249757-39-9 6-chloro-2-(hydroxymethyl)-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 
• 249757-42-4 6-chloro-2-iodo-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 
• 249757-38-8 6-chloro-2-formyl-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 
• 249757-31-1 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-phenylpurine 
• 249757-30-0 6-chloro-8-iodo-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)purine 
• 249757-28-6 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 

Relevant articles and documents

First evident generation of purin-2-yllithium: Lithiation of an 8-silyl- protected 6-chloropurine riboside as a key step for the synthesis of 2- carbon-substituted adenosines

Lithiation at the 2-position of purine ring has been accomplished for the first time by using 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D- ribofuranosyl)-8-(triisopropylsilyl)purine (7) as a substrate and LTMP as a lithiating agent. The 8-triisopropylsilyl group in 7 did not undergo anionic migration and, thus, allowed the ready generation of the C2-lithiated species by preventing deprotonation at the 8-position. The electron-withdrawing 6- chlorine atom plays an essential role to this C2-lithiation. Reactions of the lithiated species with electrophiles gave the 2-substituted products (Me, Et, i-Pr, CH(OH)C6H11, C(OH)Me2, CHO, CO2Me, and I) mostly in good yields. Ammonolysis of the 6-chlorine atom of these products (heating at 110 °C in a sealed tube with NH3/MeOH) effected simultaneous desilylation at the 8- position to give the corresponding adenosine analogues. The whole sequence provides a new and highly general method for the synthesis of 2-substituted adenosines.