Technology Process of Acetic acid (2R,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-[16-(toluene-4-sulfonyloxy)-hexadecyloxy]-tetrahydro-pyran-4-yl ester
There total 14 articles about Acetic acid (2R,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-[16-(toluene-4-sulfonyloxy)-hexadecyloxy]-tetrahydro-pyran-4-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 74 percent / Ag-silicate on alumina, 4 Angstroem molecular sieves / CH2Cl2 / 23 h / -15 - 0 °C
2: H2 / Pd(OH)2-C / ethanol; H2O / 3 h
3: methanol / 16 h
4: H2 / 10percent Pd-C / acetic acid / 24 h / 40 °C / 129010 Torr
5: pyridine / 4 h / 45 °C
6: CF3COOH / CH2Cl2 / 0.25 h
7: DBU / CH2Cl2 / 1 h / Ambient temperature
8: 4 Angstroem molecular sieves, TMSOTf / CH2Cl2 / 2 h
With
trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Ag-silicate on alumina; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid;
palladium on activated charcoal; palladium hydroxide - carbon;
In
pyridine; methanol; ethanol; dichloromethane; water; acetic acid;
DOI:10.1016/S0008-6215(98)00053-6
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 63 percent / p-TsOH / acetone / 4 h
2: 82 percent / NaH / dimethylformamide / 16 h
3: 93 percent / 80percent aq AcOH / 6 h / 60 °C
4: 74 percent / Ag-silicate on alumina, 4 Angstroem molecular sieves / CH2Cl2 / 23 h / -15 - 0 °C
5: H2 / Pd(OH)2-C / ethanol; H2O / 3 h
6: methanol / 16 h
7: H2 / 10percent Pd-C / acetic acid / 24 h / 40 °C / 129010 Torr
8: pyridine / 4 h / 45 °C
9: CF3COOH / CH2Cl2 / 0.25 h
10: DBU / CH2Cl2 / 1 h / Ambient temperature
11: 4 Angstroem molecular sieves, TMSOTf / CH2Cl2 / 2 h
With
trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Ag-silicate on alumina; hydrogen; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid;
palladium on activated charcoal; palladium hydroxide - carbon;
In
pyridine; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(98)00053-6
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 82 percent / NaH / dimethylformamide / 16 h
2: 93 percent / 80percent aq AcOH / 6 h / 60 °C
3: 74 percent / Ag-silicate on alumina, 4 Angstroem molecular sieves / CH2Cl2 / 23 h / -15 - 0 °C
4: H2 / Pd(OH)2-C / ethanol; H2O / 3 h
5: methanol / 16 h
6: H2 / 10percent Pd-C / acetic acid / 24 h / 40 °C / 129010 Torr
7: pyridine / 4 h / 45 °C
8: CF3COOH / CH2Cl2 / 0.25 h
9: DBU / CH2Cl2 / 1 h / Ambient temperature
10: 4 Angstroem molecular sieves, TMSOTf / CH2Cl2 / 2 h
With
trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Ag-silicate on alumina; hydrogen; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid;
palladium on activated charcoal; palladium hydroxide - carbon;
In
pyridine; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(98)00053-6
