(1R,2S,3R,4S)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine

Base Information

• Chemical Name: (1R,2S,3R,4S)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine
• CAS No.: 142765-06-8
• Molecular Formula: C₆₀H₆₆N₇O₁₂P
• Molecular Weight: 1108.2

Synonyms:

Chemical Property of (1R,2S,3R,4S)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4S)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine

There total 6 articles about (1R,2S,3R,4S)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine 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: 90.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + (1R,2S,3R,4S)-N6-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-2'-deoxyadenosine (142765-05-7) → (1R,2S,3R,4S)-N6-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine (142765-06-8,142796-78-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.833333h; Ambient temperature;

DOI:10.1021/jo00043a012

Reference yield:

6-fluoro-9-(2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erytropentofuranosyl)purine (135560-86-0) → (1R,2S,3R,4S)-N6-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine (142765-06-8,142796-78-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 23 mg / 2,6-lutidine, HMDS / dimethylformamide / 4 h / 90 °C

2: 100 percent / pyridine / Ambient temperature

3: 69 percent / nBu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

4: 69 percent / Li₂CO₃, 2,6-lutidine / Ambient temperature

5: 90 percent / i-Pr₂NEt / CH₂Cl₂ / 0.83 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; lithium carbonate; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00043a012

Reference yield:

(1R,2S,3R,4S)-4-Amino-1,2,3,4-tetrahydro-phenanthrene-1,2,3-triol (142765-01-3) → (1R,2S,3R,4S)-N6-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine (142765-06-8,142796-78-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 23 mg / 2,6-lutidine, HMDS / dimethylformamide / 4 h / 90 °C

2: 100 percent / pyridine / Ambient temperature

3: 69 percent / nBu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

4: 69 percent / Li₂CO₃, 2,6-lutidine / Ambient temperature

5: 90 percent / i-Pr₂NEt / CH₂Cl₂ / 0.83 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; lithium carbonate; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00043a012

upstream raw materials:

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

(1R,2S,3R,4S)-N⁶-<4-(1,2,3-Triacetoxy-1,2,3,4-tetrahydrophenanthrenyl)>-5'-O-(4,4-dimethoxytrityl)-2'-deoxyadenosine

6-fluoro-9-(2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erytropentofuranosyl)purine

(1R,2S,3R,4S)-4-Amino-1,2,3,4-tetrahydro-phenanthrene-1,2,3-triol

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