Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{methoxy-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yloxy)-methoxy-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{methoxy-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yloxy)-methoxy-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester
• CAS No.: 160343-17-9
• Molecular Formula: C₄₆H₄₇N₁₁O₁₆P₂
• Molecular Weight: 1071.89

Synonyms:

Chemical Property of Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{methoxy-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yloxy)-methoxy-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{methoxy-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yloxy)-methoxy-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester

There total 5 articles about Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{methoxy-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yloxy)-methoxy-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester 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:

3'-O-acetyl-N-benzoyl-2'-deoxyadenosine (25152-95-8) → Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{methoxy-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yloxy)-methoxy-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester (160343-17-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tetrazole, 2.) I₂ / 1.) MeCN, room temperature, overnight, 2.) 2,6-lutidine, THF, H₂O

2: 84 percent / Cl₂HCCO₂H / CH₂Cl₂ / 0.33 h

3: 1.) tetrazole, 2.) I₂ / 1.) MeCN, room temperature, 4 h, 2.) 1,6-lutidine, THF, H₂O, 2 min

With 1H-tetrazole; dichloro-acetic acid; iodine; In dichloromethane;

DOI:10.1080/15257779408011881

Reference yield:

5'-O-dimethoxytrityl-6-N-benzoyldeoxyadenosine 3'-(N,N-diisopropyl-O-methyl)phosphoramidite (84416-82-0) → Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{methoxy-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yloxy)-methoxy-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester (160343-17-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tetrazole, 2.) I₂ / 1.) MeCN, room temperature, overnight, 2.) 2,6-lutidine, THF, H₂O

2: 84 percent / Cl₂HCCO₂H / CH₂Cl₂ / 0.33 h

3: 1.) tetrazole, 2.) I₂ / 1.) MeCN, room temperature, 4 h, 2.) 1,6-lutidine, THF, H₂O, 2 min

With 1H-tetrazole; dichloro-acetic acid; iodine; In dichloromethane;

DOI:10.1080/15257779408011881

Reference yield:

N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{methoxy-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yloxy)-methoxy-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester (160343-17-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / diisopropylammonium tetrazolide

2: 1.) tetrazole, 2.) I₂ / 1.) MeCN, room temperature, overnight, 2.) 2,6-lutidine, THF, H₂O

3: 84 percent / Cl₂HCCO₂H / CH₂Cl₂ / 0.33 h

4: 1.) tetrazole, 2.) I₂ / 1.) MeCN, room temperature, 4 h, 2.) 1,6-lutidine, THF, H₂O, 2 min

With 1H-tetrazole; dichloro-acetic acid; N,N-diisopropylamine tetrazolide; iodine; In dichloromethane;

DOI:10.1080/15257779408011881

upstream raw materials:

4-nitrophenethylmethoxydiisopropylaminophosphine

Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{[(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester

3'-O-acetyl-N-benzoyl-2'-deoxyadenosine

5'-O-dimethoxytrityl-6-N-benzoyldeoxyadenosine 3'-(N,N-diisopropyl-O-methyl)phosphoramidite

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