(S_P)-5'-O-(4,4-dimethoxytrityl)thymidylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate

Base Information

• Chemical Name: (S_P)-5'-O-(4,4-dimethoxytrityl)thymidylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate
• CAS No.: 133471-19-9
• Molecular Formula: C₅₅H₆₄N₇O₁₂PSi
• Molecular Weight: 1074.21

Synonyms:

Chemical Property of (S_P)-5'-O-(4,4-dimethoxytrityl)thymidylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S_P)-5'-O-(4,4-dimethoxytrityl)thymidylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate

There total 10 articles about (S_P)-5'-O-(4,4-dimethoxytrityl)thymidylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate 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: 91.0%

6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine (51549-40-7) + (R)-Methyl-phosphonothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester S-methyl ester (129395-84-2) → (SP)-5'-O-(4,4-dimethoxytrityl)thymidylyl-(3'->5')-N6-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate (133471-19-9,133574-80-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In N,N-dimethyl-formamide; at 25 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.9b13898

Reference yield:

N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → (SP)-5'-O-(4,4-dimethoxytrityl)thymidylyl-(3'->5')-N6-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate (133471-19-9,133574-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 0 - 20 °C

2: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 0 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere; Sealed tube

With 1H-imidazole; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jacs.9b13898

Reference yield:

5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine (146578-12-3) → (SP)-5'-O-(4,4-dimethoxytrityl)thymidylyl-(3'->5')-N6-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-methylphosphonate (133471-19-9,133574-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 0 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere; Sealed tube

With toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jacs.9b13898

upstream raw materials:

(R_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>-2'-deoxyadenosine 3'-H-phosphonate

methyl iodide

triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate

6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

Downstream raw materials:

(R)-Methyl-phosphonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

(S)-Methyl-phosphonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

(S_P)-(3'->5')-2'-deoxyadenosine methylphosphonate

(R_P)-thymidylyl-(3'->5')-2'-deoxyadenosine methylphosphonate

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