N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE

Base Information

• Chemical Name: N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE
• CAS No.: 140712-80-7
• Molecular Formula: C37H35 N3 O7
• Molecular Weight: 633.701
• Mol file: 140712-80-7.mol

Synonyms:N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE

Chemical Property of N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE

Chemical Property:

• PSA: 121.14000
• LogP: 5.24290

Purity/Quality:

97% ^*data from raw suppliers

N4-Benzoyl-3''-O-(4,4''-dimethoxytrityl)-2''-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE

There total 10 articles about N4-BENZOYL-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

N4-benzoyl-3'-O-dimethoxytrityl-5'-O-levulinyl-2'-deoxycytidine → N4-benzoyl-3'-O-dimethoxytrityl-2'-deoxycytidine (140712-80-7)

Guidance literature:

With pyridine; acetic acid; hydrazine; In water; at 20 ℃; for 2h; chemoselective reaction;

DOI:10.1021/op050253i

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) + N4-benzoyl-2'-deoxycytidine (4836-13-9) → 4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (67219-55-0) + N4-benzoyl-O3',O5'-bis-(4,4'-dimethoxy-trityl)-2'-deoxy-cytidine (107744-25-2) + N4-benzoyl-3'-O-dimethoxytrityl-2'-deoxycytidine (140712-80-7)

Guidance literature:

4,4'-dimethoxytrityl chloride; N₄-benzoyl-2'-deoxycytidine; In pyridine; at 20 ℃; for 6h;

With sodium hydrogencarbonate; In water; ethyl acetate; for 2h;

Reference yield:

N4-benzoyl-2'-deoxycytidine (4836-13-9) → N4-benzoyl-3'-O-dimethoxytrityl-2'-deoxycytidine (140712-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂

3: tetrabutylammonium fluoride / tetrahydrofuran

With pyridine; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;

DOI:10.1081/NCN-200033912

upstream raw materials:

N-{1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

N-(1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

N₄-benzoyl-2'-deoxycytidine

N-(1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Downstream raw materials:

{(2R,3S,5R)-5-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-ylmethoxymethyl}-phosphonic acid monomethyl ester

Refernces

• 1、 Rejman, Dominik,Masojidkova, Milena,Rosenberg, Ivan. "Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides". . p. 1683 - 1705. Retrieved 2007/10/03.
• 2、 Esipov, Dmitriy S.,Esipova, Olga V.,Korobko, Vyacheslav G.. "Synthesis of 3'-azido-3'-deoxythymidine-terminated oligonucleotide". . p. 1697 - 1704. Retrieved 2007/10/03.