Technology Process of Benzoic acid (2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-benzyloxymethyl-5-cyanomethoxy-tetrahydro-pyran-3-yl ester
There total 10 articles about Benzoic acid (2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-benzyloxymethyl-5-cyanomethoxy-tetrahydro-pyran-3-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 93 percent / p-TsOH*H2O / acetonitrile / Ambient temperature
2: 86 percent / NaH / dimethylformamide / 0 °C
3: 70 percent / NaCNBH3, molecular sieves 4 Angstroem, HCl / tetrahydrofuran; diethyl ether / 1.) -5 deg C, 2 h, 2.) room temperatuere, overnight.
4: 57 percent / AgOTf, molecular sieves 4 Angstroem, Br2 / CH2Cl2 / 1 h / -30 °C
5: 85 percent / NaCNBH3, molecular sieves 4 Angstroem / tetrahydrofuran; diethyl ether / 3 h / Ambient temperature
6: 1.) NaH / 1.) CH3CN, room temperature, 2 h, 2.) CH2Cl2, from -18 deg C to room temperature, 4 h.
With
hydrogenchloride; 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(97)00142-0
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 91 percent / Py / Ambient temperature
2: 57 percent / AgOTf, molecular sieves 4 Angstroem, Br2 / CH2Cl2 / 1 h / -30 °C
3: 85 percent / NaCNBH3, molecular sieves 4 Angstroem / tetrahydrofuran; diethyl ether / 3 h / Ambient temperature
4: 1.) NaH / 1.) CH3CN, room temperature, 2 h, 2.) CH2Cl2, from -18 deg C to room temperature, 4 h.
With
pyridine; 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0008-6215(97)00142-0
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 93 percent / p-TsOH*H2O / acetonitrile / Ambient temperature
2: 86 percent / NaH / dimethylformamide / 0 °C
3: 70 percent / NaCNBH3, molecular sieves 4 Angstroem, HCl / tetrahydrofuran; diethyl ether / 1.) -5 deg C, 2 h, 2.) room temperatuere, overnight.
4: 57 percent / AgOTf, molecular sieves 4 Angstroem, Br2 / CH2Cl2 / 1 h / -30 °C
5: 85 percent / NaCNBH3, molecular sieves 4 Angstroem / tetrahydrofuran; diethyl ether / 3 h / Ambient temperature
6: 1.) NaH / 1.) CH3CN, room temperature, 2 h, 2.) CH2Cl2, from -18 deg C to room temperature, 4 h.
With
hydrogenchloride; 4 A molecular sieve; bromine; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(97)00142-0
