Technology Process of 2-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethanol
There total 9 articles about 2-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-ethanol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
((2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane;
With
9-borabicyclo[3.3.1]nonane dimer;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 2h;
With
dihydrogen peroxide; sodium hydrogencarbonate;
In
tetrahydrofuran; water;
at 20 ℃;
for 0.5h;
Further stages.;
DOI:10.1021/ol015798l
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 2,6-lutidine / CH2Cl2 / 5 h / 0 °C
1.2: 85 percent / CSA / CH2Cl2; methanol / 1 h / 0 °C
2.1: SO3*Pyr; Et3N / dimethylsulfoxide; CH2Cl2 / 1 h / 20 °C
3.1: 5.87 g / NaHMDS / tetrahydrofuran / 0.33 h / 0 °C
4.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C
4.2: 95 percent / NaHCO3; H2O2 / tetrahydrofuran; H2O / 0.5 h / 20 °C
With
2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO3 complex; sodium hexamethyldisilazane; triethylamine;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
3.1: Wittig reaction;
DOI:10.1021/ol015798l
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: NaH / dimethylformamide; various solvent(s) / 0 - 20 °C
2.1: 1.63 g / CSA / CH2Cl2; methanol / 20 h / 0 °C
3.1: 2,6-lutidine / CH2Cl2 / 5 h / 0 °C
3.2: 85 percent / CSA / CH2Cl2; methanol / 1 h / 0 °C
4.1: SO3*Pyr; Et3N / dimethylsulfoxide; CH2Cl2 / 1 h / 20 °C
5.1: 5.87 g / NaHMDS / tetrahydrofuran / 0.33 h / 0 °C
6.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C
6.2: 95 percent / NaHCO3; H2O2 / tetrahydrofuran; H2O / 0.5 h / 20 °C
With
2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO3 complex; camphor-10-sulfonic acid; sodium hexamethyldisilazane; sodium hydride; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
5.1: Wittig reaction;
DOI:10.1021/ol015798l
