Technology Process of (2R,3S,4R,5R)-5-benzyloxy-3,4-isopropylidenedioxy-1-phenyl-4-vinylheptan-2-ol
There total 12 articles about (2R,3S,4R,5R)-5-benzyloxy-3,4-isopropylidenedioxy-1-phenyl-4-vinylheptan-2-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
copper(I) bromide dimethylsulfide complex; dimethylsulfide;
In
tetrahydrofuran;
at 0 ℃;
- Guidance literature:
-
Multi-step reaction with 11 steps
1: pyridinium chlorochromate; molecular sieves 4 Angstroem / CH2Cl2 / 10 h / 20 °C
2: tetrahydrofuran / 1 h / -18 °C
3: aq. AcOH / 11 h / 80 °C
4: 5.60 g / N-iodosuccinimide; n-Bu4NI / CH2Cl2 / 20 h / 20 °C
5: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr
6: 91 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
7: DMAP; pyridine / 4 h / Heating
8: NaH / dimethylformamide / 8 h / 20 °C
9: 6.59 g / CSA / methanol / 48 h / 20 °C
10: 96 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
11: 14 percent / tetrahydrofuran / 20 °C
With
pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; acetic acid; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
10: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703
- Guidance literature:
-
Multi-step reaction with 9 steps
1: aq. AcOH / 11 h / 80 °C
2: 5.60 g / N-iodosuccinimide; n-Bu4NI / CH2Cl2 / 20 h / 20 °C
3: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr
4: 91 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
5: DMAP; pyridine / 4 h / Heating
6: NaH / dimethylformamide / 8 h / 20 °C
7: 6.59 g / CSA / methanol / 48 h / 20 °C
8: 96 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
9: 14 percent / tetrahydrofuran / 20 °C
With
pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; acetic acid;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
8: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703
