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

Base Information

Chemical Name: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
CAS No.:228394-79-4
Molecular Formula:C₃₂H₃₇N₅O₁₀
Molecular Weight:651.673
Hs Code.:

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

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 13 articles about 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 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:

: 228394-78-3
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

: 228394-79-4
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

Guidance literature:: With potassium carbonate; In methanol; dichloromethane; for 22h;
DOI:10.1021/ja990274q

Reference yield:

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 228394-79-4
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

Guidance literature:: Multi-step reaction with 11 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

11: 0.02 M K₂CO₃ / methanol; CH₂Cl₂ / 22 h

With pyridine; hydrogenchloride; methanol; ammonium hydroxide; iodonium(di-γ-collidine) perchlorate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; potassium carbonate; triethylamine tris(hydrogen fluoride); triethylamine; In methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ja990274q

Reference yield:

: 146558-05-6
2-N-acetyl-6-O-(diphenylcarbamoyl)guanine

: 228394-79-4
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

Guidance literature:: Multi-step reaction with 5 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

5: 0.02 M K₂CO₃ / methanol; CH₂Cl₂ / 22 h

With pyridine; ammonium hydroxide; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; triethylamine tris(hydrogen fluoride); In methanol; dichloromethane; toluene;
DOI:10.1021/ja990274q