Technology Process of (2R,3R,4S,5R,6S)-5,6-Bis-benzyloxy-4-heptyloxy-2-isobutyl-tetrahydro-pyran-3-ol
There total 12 articles about (2R,3R,4S,5R,6S)-5,6-Bis-benzyloxy-4-heptyloxy-2-isobutyl-tetrahydro-pyran-3-ol 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:
- Guidance literature:
-
With
2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
dichloromethane;
at 25 ℃;
for 1.5h;
DOI:10.1021/jm970709p
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 100 percent / NaH / dimethylformamide / 2.25 h / 0 - 25 °C
2: 60percent aq. AcOH / 15 h / 90 °C
3: AcCl / benzene / 15 h / 80 °C
4: 88 percent / p-TsOH*H2O / benzene / 15 h / 110 °C
5: 100 percent / NaH / dimethylformamide / 14 h / 25 °C
6: DIBAH / hexane; toluene / 1 h / 0 °C
7: DMSO, oxalyl chloride / 0.67 h / -78 °C
8: 1.) n-BuLi / 1.) THF, pentane, 25 deg C, 30 min, 2.) THF, pentane, 0 deg C, 3 h
9: 77 percent / benzenesulfonyl hydrazide, aq. NaOH / 2-methoxy-ethanol / Heating
10: 87 percent / DDQ / CH2Cl2 / 1.5 h / 25 °C
With
sodium hydroxide; n-butyllithium; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; acetyl chloride; benzenesufonyl hydrazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
hexane; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jm970709p
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 100 percent / NaH / dimethylformamide / 14 h / 25 °C
2: DIBAH / hexane; toluene / 1 h / 0 °C
3: DMSO, oxalyl chloride / 0.67 h / -78 °C
4: 1.) n-BuLi / 1.) THF, pentane, 25 deg C, 30 min, 2.) THF, pentane, 0 deg C, 3 h
5: 77 percent / benzenesulfonyl hydrazide, aq. NaOH / 2-methoxy-ethanol / Heating
6: 87 percent / DDQ / CH2Cl2 / 1.5 h / 25 °C
With
sodium hydroxide; n-butyllithium; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; benzenesufonyl hydrazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
hexane; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm970709p
