Technology Process of Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester
There total 5 articles about Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester which
guide to synthetic route it.
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synthetic route:
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183660-36-8
Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester
- Guidance literature:
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Multi-step reaction with 5 steps
1: 82 percent / conc. aq. HCl / methanol / 6 h / Heating
2: 86 percent / aq. NaHCO3 / acetone; toluene / 4 °C
3: 78 percent / pyridine / dimethylformamide / Ambient temperature
4: 76 percent / n-Bu4NI, (Me3Si)2NLi / dimethylsulfoxide; tetrahydrofuran / 0.5 h / Ambient temperature
5: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -76 deg C, 2.) CH2Cl2
With
pyridine; hydrogenchloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; ozone; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja9612817
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183660-36-8
Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester
- Guidance literature:
-
Multi-step reaction with 3 steps
1: 78 percent / pyridine / dimethylformamide / Ambient temperature
2: 76 percent / n-Bu4NI, (Me3Si)2NLi / dimethylsulfoxide; tetrahydrofuran / 0.5 h / Ambient temperature
3: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -76 deg C, 2.) CH2Cl2
With
pyridine; tetra-(n-butyl)ammonium iodide; ozone; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja9612817
-
-
183660-36-8
Acetic acid (1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-3-[(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-benzyloxycarbonylamino-6-(benzyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-(2-oxo-ethoxy)-cyclohexyl ester
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 86 percent / aq. NaHCO3 / acetone; toluene / 4 °C
2: 78 percent / pyridine / dimethylformamide / Ambient temperature
3: 76 percent / n-Bu4NI, (Me3Si)2NLi / dimethylsulfoxide; tetrahydrofuran / 0.5 h / Ambient temperature
4: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -76 deg C, 2.) CH2Cl2
With
pyridine; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; ozone; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja9612817