N⁴-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite)

Base Information

• Chemical Name: N⁴-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite)
• CAS No.: 115383-35-2
• Molecular Formula: C₃₇H₆₂N₅O₇PSi₂
• Molecular Weight: 776.073

Synonyms:N⁴-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite)

Chemical Property of N⁴-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite)

Chemical Property:

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Technology Process of N⁴-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite)

There total 1 articles about N⁴-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite) 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: 82.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N4-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine (72409-40-6) → N4-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite) (115383-35-2)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo00251a010

Reference yield:

N6-Benzoyl-5'-O-(monomethoxytrityl)adenosine (69504-00-3) + N4-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite) (115383-35-2) + N2-benzoyl-O6-(p-nitrophenylethyl)-2',3'-bis-O-(tert-butyldimethylsilyl)guanosine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite) (115363-51-4) → C28H35N11O18P2(2-)*2Na(1+) + C29H35N13O18P2(2-)*2Na(1+) + C29H35N13O18P2(2-)*2Na(1+) (111772-32-8) + C30H35N15O18P2(2-)*2Na(1+)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo00251a010

Reference yield:

N6-Benzoyl-5'-O-(monomethoxytrityl)adenosine (69504-00-3) + N4-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine 5'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite) (115383-35-2) → C99H127N13O22P2Si4 (115363-60-5) + Phosphoric acid (2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester bis-(2-cyano-ethyl) ester (115363-65-0) + C59H92N7O14PSi4 (115363-67-2)

Guidance literature:

With 1H-tetrazole; 2,4,6-trimethyl-pyridine; water; iodine; Multistep reaction; 1.) THF, RT, 1 h, 2.) 5 min;

DOI:10.1021/jo00251a010

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

N⁴-benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)cytidine

Downstream raw materials:

C₂₉H₃₅N₁₃O₁₈P₂^(2-)*2Na⁽¹⁺⁾

C₇₉H₁₁₁N₁₃O₂₁P₂Si₄

C₈₈H₁₁₈N₁₆O₂₃P₂Si₄

C₈₈H₁₁₈N₁₆O₂₃P₂Si₄

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