Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 228394-78-3
• Molecular Formula: C₃₆H₄₁N₅O₁₂
• Molecular Weight: 735.748

Synonyms:Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

Chemical Property:

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Useful:

Technology Process of Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester

There total 12 articles about Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-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:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (228394-78-3)

Guidance literature:

Multi-step reaction with 10 steps

1: HCl / CH₂Cl₂ / 2 h / 0 °C

2: CH₂Cl₂ / 18 h

3: NaOCH₃, CH₃OH / 2 h

4: pyridine, Et₃N / CH₂Cl₂ / 4 h

5: IDCP / 1,2-dichloro-ethane; diethyl ether / 3 h

6: 15 h

7: TMSOTf / toluene / 3 h / 80 °C

8: 3HF*Et₃N, pyridine / 6 h

9: 25 percent aq. NH₄OH / methanol / 24 h / 60 °C

10: pyridine / 6 h

With pyridine; hydrogenchloride; methanol; ammonium hydroxide; iodonium(di-γ-collidine) perchlorate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; triethylamine tris(hydrogen fluoride); triethylamine; In methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ja990274q

Reference yield:

2-N-acetyl-6-O-(diphenylcarbamoyl)guanine (146558-05-6) → Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (228394-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1: TMSOTf / toluene / 3 h / 80 °C

2: 3HF*Et₃N, pyridine / 6 h

3: 25 percent aq. NH₄OH / methanol / 24 h / 60 °C

4: pyridine / 6 h

With pyridine; ammonium hydroxide; trimethylsilyl trifluoromethanesulfonate; triethylamine tris(hydrogen fluoride); In methanol; toluene;

DOI:10.1021/ja990274q

Reference yield:

N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) → Acetic acid (2R,3R,4R,5R)-4-((2S,3S,4R,5R,6S)-5-acetoxy-3,4-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-acetoxymethyl-2-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (228394-78-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1,2-dichloro-ethane / 0.25 h / 80 °C

2: TMSOTf / toluene / 3 h / 80 °C

3: 3HF*Et₃N, pyridine / 6 h

4: 25 percent aq. NH₄OH / methanol / 24 h / 60 °C

5: pyridine / 6 h

With pyridine; ammonium hydroxide; trimethylsilyl trifluoromethanesulfonate; triethylamine tris(hydrogen fluoride); In methanol; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ja990274q

upstream raw materials:

acetic anhydride

2-Amino-9-[(2R,3R,4S,5R)-4-((2S,3S,4R,5R,6S)-3,4-bis-benzyloxy-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2-N-acetyl-6-O-(diphenylcarbamoyl)guanine

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methyl-6-[(2R,3R,4R,5R)-5-(6-oxo-2-sulfoamino-1,6-dihydro-purin-9-yl)-4-sulfooxy-2-sulfooxymethyl-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4R,5S,6S)-6-[(2R,3R,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-4-sulfooxy-2-sulfooxymethyl-tetrahydro-furan-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4R,5S,6S)-6-[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

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