Technology Process of (2S,3S,4S,5R,6S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-phenoxy)-4,5-bis-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
There total 10 articles about (2S,3S,4S,5R,6S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-phenoxy)-4,5-bis-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl 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:
-
-
180274-58-2
(2S,3S,4S,5R,6S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-phenoxy)-4,5-bis-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 73 percent / p-TSA / 1 h / Ambient temperature
2: pyridine
3: MeOH, camphorsulfonic acid / Ambient temperature
4: 99 percent / imidazole / dimethylformamide
5: 42 percent / AgOTf, molecular sieves 4 Angstroem / CH2Cl2 / 1.) r.t., 40 min, 2.) 0 deg C, 1.5 h; r.t., 1 day
6: 89 percent / TBAF, AcOH / tetrahydrofuran / 120 h / Ambient temperature
7: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH2Cl2, -78 deg C, 30 min, 2.) 35 min
8: aq. NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol
9: ethyl acetate; diethyl ether
With
pyridine; 1H-imidazole; methanol; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
toluene-4-sulfonic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
-
-
180274-58-2
(2S,3S,4S,5R,6S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-phenoxy)-4,5-bis-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 42 percent / AgOTf, molecular sieves 4 Angstroem / CH2Cl2 / 1.) r.t., 40 min, 2.) 0 deg C, 1.5 h; r.t., 1 day
2: 89 percent / TBAF, AcOH / tetrahydrofuran / 120 h / Ambient temperature
3: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH2Cl2, -78 deg C, 30 min, 2.) 35 min
4: aq. NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol
5: ethyl acetate; diethyl ether
With
sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; tert-butyl alcohol;
-
-
180274-58-2
(2S,3S,4S,5R,6S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-phenoxy)-4,5-bis-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
- Guidance literature:
-
Multi-step reaction with 8 steps
1: pyridine
2: MeOH, camphorsulfonic acid / Ambient temperature
3: 99 percent / imidazole / dimethylformamide
4: 42 percent / AgOTf, molecular sieves 4 Angstroem / CH2Cl2 / 1.) r.t., 40 min, 2.) 0 deg C, 1.5 h; r.t., 1 day
5: 89 percent / TBAF, AcOH / tetrahydrofuran / 120 h / Ambient temperature
6: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH2Cl2, -78 deg C, 30 min, 2.) 35 min
7: aq. NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol
8: ethyl acetate; diethyl ether
With
pyridine; 1H-imidazole; methanol; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;