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

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-hydroxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester
• CAS No.: 160343-16-8
• Molecular Formula: C₃₇H₃₇N₁₀O₁₁P
• Molecular Weight: 828.735

Synonyms: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

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-hydroxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester

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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-hydroxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester

There total 4 articles about 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 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: 84.0%

Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-({(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxy}-methoxy-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester (160343-15-7) → 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 (160343-16-8)

Guidance literature:

With dichloro-acetic acid; In dichloromethane; for 0.333333h;

DOI:10.1080/15257779408011881

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-hydroxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester (160343-16-8)

Guidance literature:

Multi-step reaction with 2 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

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-hydroxymethyl-tetrahydro-furan-3-yloxy]-methoxy-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester (160343-16-8)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1080/15257779408011881

upstream raw materials:

Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-({(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-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

N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

Downstream raw materials:

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

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