methyl (N⁴-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N⁶,O^2',O^3'-tribenzoyl)adenosine

Base Information

• Chemical Name: methyl (N⁴-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N⁶,O^2',O^3'-tribenzoyl)adenosine
• CAS No.: 88867-00-9
• Molecular Formula: C₅₄H₅₇N₈O₁₅PSi
• Molecular Weight: 1117.15

Synonyms:methyl (N⁴-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N⁶,O^2',O^3'-tribenzoyl)adenosine

Chemical Property of methyl (N⁴-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N⁶,O^2',O^3'-tribenzoyl)adenosine

Chemical Property:

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Technology Process of methyl (N⁴-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N⁶,O^2',O^3'-tribenzoyl)adenosine

There total 1 articles about methyl (N⁴-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N⁶,O^2',O^3'-tribenzoyl)adenosine 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: 73.0%

methyl(N4-benzoyl-2'-O-t-butyldimethylsilyl-5'-O-monomethoxytrityl)-cytidylyl (3'-> 5') (N6,O2',O3'-tribenzoyl) adenosine → methyl (N4-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N6,O2',O3'-tribenzoyl)adenosine (88867-00-9)

Guidance literature:

With benzenesulfonic acid; In ethanol; chloroform; at 5 ℃; for 8h;

DOI:10.1016/0040-4020(84)85106-6

Reference yield:

methyl (N4-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N6,O2',O3'-tribenzoyl)adenosine (88867-00-9) → 2'-O-(N-acetyl-L-phenylalanyl)-pCpA

Guidance literature:

Multi-step reaction with 5 steps

1: 33 percent / 1.) POCl₃, collidine / 1.) THF, -78 deg C, 1 h; 2.) 0 deg C, 30 min

2: 83 percent / 1 M tetrabutylammonium fluoride / tetrahydrofuran / 7 h / Ambient temperature

3: 1.) 1,1'-carbonyldiimidazole / 1.) DMSO, r.t., 20 min; 2.) DMSO, 25 deg C, 70 h

4: 0.1 N HCl / 24 h / 25 °C

5: 1.) 10percent Pd/C / 1.) EtOH-0.01 N AcOH, 25 deg C, 20 h; 2.) DMSO, 25 deg C, 16 h

With 2,3,5-trimethyl-pyridine; hydrogenchloride; tetrabutyl ammonium fluoride; 1,1'-carbonyldiimidazole; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/0040-4020(84)85106-6

Reference yield:

methyl (N4-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N6,O2',O3'-tribenzoyl)adenosine (88867-00-9) → C39H45N9O17P2

Guidance literature:

Multi-step reaction with 4 steps

1: 33 percent / 1.) POCl₃, collidine / 1.) THF, -78 deg C, 1 h; 2.) 0 deg C, 30 min

2: 83 percent / 1 M tetrabutylammonium fluoride / tetrahydrofuran / 7 h / Ambient temperature

3: 43 percent / 1.) 1,1'-carbonyldiimidazole / 1.) DMSO, r.t., 20 min; 2.) DMSO, 25 deg C, 20 h

4: 1.) 1,1'-carbonyldiimidazole / 1.) DMSO, r.t., 20 min; 2.) DMSO, 25 deg C, 70 h

With 2,3,5-trimethyl-pyridine; tetrabutyl ammonium fluoride; 1,1'-carbonyldiimidazole; trichlorophosphate; In tetrahydrofuran;

DOI:10.1016/0040-4020(84)85106-6

Downstream raw materials:

cytidylyl (3'-> 5') adenosine 5'-monophosphate

N⁴-(N-acetyl-D,L-phenylalanyl) cytidylyl (3'->5') adenosine 5'-phosphate

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