1054635-91-4

Upstream product

• 147490-70-8 2-N-(Phenacetyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)guanosine 
• 263008-90-8 1-(4-Chlorophenyl)-4-ethoxy-1,2,5,6-tetrahydropyridine 
• 3592-25-4 1,5-dichloropentan-3-one 
• 263008-89-5 1-(4-Chlorophenyl)-4,4-diethoxypiperidine 
• 113759-96-9 1-(4-chlorophenyl)piperidin-4-one 
• 119836-12-3 4-hydroxy-1-(4-chlorophenyl)piperidine 
• 106-47-8 4-chloro-aniline 
• 72548-31-3 1,5-Dichloropentan-3-ol 

Downstream Products

• 263009-04-7 2'-O-[1-(4-Chlorophenyl)-4-ethoxypiperidin-4-yl]guanosine 
• 263009-03-6 2'-O-[1-(4-Chlorophenyl)-4-ethoxypiperidin-4-yl]-2-N-(phenylacetyl)guanosine 

Relevant academic research and scientific papers

Synthesis of 3′,5′-cyclic diguanylic acid (cdiGMP) using 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl as a protecting group for 2′-hydroxy functions of ribonucleosides

We herein report a convenient synthesis of 3′,5′-cyclic diguanylic acid via the modified H-phosphonate approach. The 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) group was used as protecting group for the 2′-hydroxy functions of ribonucleosides. Complete unblocking of the fully protected 3′,5′-cyclic diguanylic acid gave cdiGMP as a homogeneous compound in an excellent yield. Copyright Taylor & Francis Group, LLC.

Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides

The comparative rates of acid-catalysed removal often 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined. The Royal Society of Chemistry 2000.