82893-26-3

Basic information

• Product Name: 3-Adenylic acid, N-benzoyl-5-O-(bis(4-methoxyphenyl)phenylmethyl)-2-deoxy-, mono(4-chlorophenyl) ester, compd. with N,N-diethylethanamine (1:1)
• CAS NO: 82893-26-3
• Molecular Weight: 949.44
• Mol File: 82893-26-3.mol

Chemical Properties

• CAS DataBase Reference: 3-Adenylic acid, N-benzoyl-5-O-(bis(4-methoxyphenyl)phenylmethyl)-2-deoxy-, mono(4-chlorophenyl) ester, compd. with N,N-diethylethanamine (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Adenylic acid, N-benzoyl-5-O-(bis(4-methoxyphenyl)phenylmethyl)-2-deoxy-, mono(4-chlorophenyl) ester, compd. with N,N-diethylethanamine (1:1)(82893-26-3)
• EPA Substance Registry System: 3-Adenylic acid, N-benzoyl-5-O-(bis(4-methoxyphenyl)phenylmethyl)-2-deoxy-, mono(4-chlorophenyl) ester, compd. with N,N-diethylethanamine (1:1)(82893-26-3)

Safety Data

• Hazardous Substances Data: 82893-26-3(Hazardous Substances Data)

Upstream product

• 65062-69-3 p-chlorophenyl phosphoroditriazolide 
• 64325-78-6 N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 
• 121-44-8 triethylamine 
• 57777-86-3 5'-O-(dimethoxytrityl)-N-benzoyladenine 3'-(p-chlorophenylcyanoethyl phosphate) 
• 4546-72-9 N₆-benzoyl-2'-deoxyadenosine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 

Downstream Products

• 93403-63-5 C₅₃H₄₉ClN₅O₁₁PS 
• 82893-28-5 (S_P)-N⁶-Benzoyl-O^P-(4-chlorphenyl)-2'-desoxyadenylyl-(3'-5')-3'-O-acetyl-N⁶-benzoyl-2'-desoxyadenosin 
• 82893-28-5 (R_P)-N⁶-Benzoyl-O^P-(4-chlorphenyl)-2'-desoxyadenylyl-(3'-5')-3'-O-acetyl-N⁶-benzoyl-2'-desoxyadenosin 
• 67221-75-4 <(MeO)2Tr>A^bzpTOAc 

Relevant articles and documents

31P NMR Study of the Mechanism of Activation and Coupling Reactions in the Synthesis of Oligodeoxyribonucleotides by the Phosphotriester Method

The phosphotriester method provides a rapid and convenient procedure for synthesizing oligonucleotides.The mechanism has been revealed and intermediates have been identified by 31P NMR methodology.It was found that reaction of a 5'-protected nucleoside 3'-(p-chlorophenyl phosphate) with mesitylenesulfonyl chloride (MSCl) or 1-(mesitylyl-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) in anhydrous pyridine yields only two products within 5 min, the sulfonic acid-phosphate mixed anhydride 2 and the (3'-3') symmetrical pyrophosphate tetraester 3 which can be isolated as a mixture.Reaction of 2 and 3 with 3'-O-acetylthymidine yields the phosphotriester dimer NpTOAc.The reaction rate and yield of dimers are closely dependent on the presence of catalysts.The reaction finished within minutes when tetrazole or 3-nitro-1,2,4-triazole was used.On the contrary, the reaction completed in hours when imidazole or 1,2,4-triazole was used as catalysts.The possible mechanisms are explored and discussed in detail.

Synthesis and Designation of the Diastereomeric Forms of Fully Protected 2'-Deoxyadenylyl-(3'-5')-2'-deoxyadenosine

The synthesis of the fully protected 2'-deoxyadenylyl-(3'-5')-2'-deoxyadenosine 3a is reported.Due to the chiral phosphotriester group 3a exists in two diasteromeric forms (3aA and 3aB) which could be distinguished by TLC and HPLC as well as 1H and 31P NMR spectroscopy.The absolute configuration as RP (3aA) and SP (3aB) is proposed on the basis of NMR data and chromatographic properties in combination with space filling models.