Technology Process of 1-[(2R,4aR,6R,7R,8S,8aR)-8-Benzyloxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-6-(4-methoxy-benzyloxy)-hexan-3-one
There total 15 articles about 1-[(2R,4aR,6R,7R,8S,8aR)-8-Benzyloxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-6-(4-methoxy-benzyloxy)-hexan-3-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
DOI:10.1021/ja973287h
- Guidance literature:
-
Multi-step reaction with 7 steps
1: (+/-)-camphorsulfonic acid, 4 Angstroem molecular sieves / CH2Cl2 / 3.5 h / Ambient temperature
2: 93 percent / Et3N
3: 87 percent / 9-BBN, H2O2
4: 90 percent / oxalyl chloride, DMSO, Et3N
5: 1.) t-BuLi / 1.) Et2O, pentane, -78 deg C, 20 min, 2.) Et2O, pentane, -78 deg C, 15 min
6: 89 percent / Dess-Martin periodinane
7: 86 percent / TBAF / tetrahydrofuran
With
9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; Dess-Martin periodane; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/ja973287h
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 91 percent / TsOH / methanol
2: acetonitrile / 2.5 h / 70 - 80 °C
3: TMSOTf / acetonitrile / 12 h / Ambient temperature
4: (+/-)-camphorsulfonic acid, 4 Angstroem molecular sieves / CH2Cl2 / 3.5 h / Ambient temperature
5: 93 percent / Et3N
6: 87 percent / 9-BBN, H2O2
7: 90 percent / oxalyl chloride, DMSO, Et3N
8: 1.) t-BuLi / 1.) Et2O, pentane, -78 deg C, 20 min, 2.) Et2O, pentane, -78 deg C, 15 min
9: 89 percent / Dess-Martin periodinane
10: 86 percent / TBAF / tetrahydrofuran
With
9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/ja973287h
![1-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-6-(4-methoxy-benzyloxy)-hexan-3-one](/Databaselist/images/loading.webp)
