Technology Process of (2S,3S,6R,7R)-7-(t-butyldiphenylsilyloxy)-6-methoxymethyloxy-2,3-epoxy-henicosan-1-ol
There total 7 articles about (2S,3S,6R,7R)-7-(t-butyldiphenylsilyloxy)-6-methoxymethyloxy-2,3-epoxy-henicosan-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve;
titanium(IV) isopropylate;
In
2,2,4-trimethylpentane; dichloromethane;
at -23 ℃;
for 18h;
DOI:10.1021/jo060970q
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: AD-mix-β; methanesulfonamide / H2O; 2-methyl-propan-2-ol / 19 h / 0 °C
1.2: KOH / methanol / 2 h / 60 °C
1.3: 74 percent / p-TsOH*H2O / CH2Cl2 / 1.5 h / 20 °C
2.1: 88 percent / 2,6-lutidine / CH2Cl2; toluene / 72 h / 20 °C
3.1: diisobutylaluminum hydride / CH2Cl2; hexane / 1 h / -78 °C
3.2: 91 percent / toluene / 5 h / 65 - 70 °C
4.1: 90 percent / ethyldiisopropylamine / CH2Cl2 / 120 h / 20 °C
5.1: 96 percent / diisobutyllithium hydride / toluene; hexane / 1 h / -78 °C
6.1: 64 percent / L-(+)-diethyl tartrate; molecular sieves 4 Angstroem; t-BuO2H / Ti(O-iPr)4 / CH2Cl2; 2,2,4-trimethyl-pentane / 18 h / -23 °C
With
2,6-dimethylpyridine; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; methanesulfonamide; 4 A molecular sieve; AD-mix-β; diisobutyllithium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine;
titanium(IV) isopropylate;
In
2,2,4-trimethylpentane; hexane; dichloromethane; water; toluene; tert-butyl alcohol;
1.1: Sharpless asymmetric dihydroxylation / 3.2: Wittig reaction;
DOI:10.1021/jo060970q
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 88 percent / 2,6-lutidine / CH2Cl2; toluene / 72 h / 20 °C
2.1: diisobutylaluminum hydride / CH2Cl2; hexane / 1 h / -78 °C
2.2: 91 percent / toluene / 5 h / 65 - 70 °C
3.1: 90 percent / ethyldiisopropylamine / CH2Cl2 / 120 h / 20 °C
4.1: 96 percent / diisobutyllithium hydride / toluene; hexane / 1 h / -78 °C
5.1: 64 percent / L-(+)-diethyl tartrate; molecular sieves 4 Angstroem; t-BuO2H / Ti(O-iPr)4 / CH2Cl2; 2,2,4-trimethyl-pentane / 18 h / -23 °C
With
2,6-dimethylpyridine; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; diisobutyllithium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine;
titanium(IV) isopropylate;
In
2,2,4-trimethylpentane; hexane; dichloromethane; toluene;
2.2: Wittig reaction;
DOI:10.1021/jo060970q
