Technology Process of 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
There total 14 articles about 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 which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 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
12: SO3*pyr, pyridine / 4 h / 55 °C
With
pyridine; hydrogenchloride; methanol; ammonium hydroxide; pyridine-SO3 complex; 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
- Guidance literature:
-
Multi-step reaction with 6 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
6: SO3*pyr, pyridine / 4 h / 55 °C
With
pyridine; ammonium hydroxide; pyridine-SO3 complex; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; triethylamine tris(hydrogen fluoride);
In
methanol; dichloromethane; toluene;
DOI:10.1021/ja990274q
- Guidance literature:
-
Multi-step reaction with 7 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
6: 0.02 M K2CO3 / methanol; CH2Cl2 / 22 h
7: SO3*pyr, pyridine / 4 h / 55 °C
With
pyridine; ammonium hydroxide; pyridine-SO3 complex; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; triethylamine tris(hydrogen fluoride);
In
methanol; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ja990274q
