Technology Process of (3R,4R,6S)-8-benzyloxy-3-methyl-6-(tert-butyldimethylsilyl)oxyoct-1-en-4-ol
There total 8 articles about (3R,4R,6S)-8-benzyloxy-3-methyl-6-(tert-butyldimethylsilyl)oxyoct-1-en-4-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:
-
(Z)-2-Butene;
With
n-butyllithium; potassium tert-butylate;
In
tetrahydrofuran; hexane;
at -50 ℃;
for 0.5h;
With
(-)-B-methoxydiisopinocamphenylborane;
In
tetrahydrofuran; diethyl ether; hexane;
at -78 ℃;
for 0.5h;
(3S)-5-benzyloxy-3-(tert-butyldimethylsilyl)oxypentanal;
With
boron trifluoride diethyl etherate;
In
tetrahydrofuran; diethyl ether; hexane;
at -78 ℃;
for 24h;
DOI:10.1021/jo0503862
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 99 percent / H2 / Ru2Cl4[(S)-BIMAP]Et3N / methanol / 60 h / 2585.74 Torr
2.1: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / -78 °C
3.1: 100 percent / DIBAL-H / toluene / 2 h / -78 °C
4.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -50 °C
4.2: (-)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane; diethyl ether / 0.5 h / -78 °C
4.3: 47 percent / BF3*OEt2 / tetrahydrofuran; hexane; diethyl ether / 24 h / -78 °C
With
2,6-dimethylpyridine; n-butyllithium; potassium tert-butylate; hydrogen; diisobutylaluminium hydride;
Ru2Cl4-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt3;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
4.3: Brown asymmetric crotylation;
DOI:10.1021/jo0503862
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: NaH / tetrahydrofuran / 0.75 h / 0 °C
1.2: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -25 °C
1.3: 56 percent / tetrahydrofuran; hexane / 1 h / -25 °C
2.1: 99 percent / H2 / Ru2Cl4[(S)-BIMAP]Et3N / methanol / 60 h / 2585.74 Torr
3.1: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / -78 °C
4.1: 100 percent / DIBAL-H / toluene / 2 h / -78 °C
5.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -50 °C
5.2: (-)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane; diethyl ether / 0.5 h / -78 °C
5.3: 47 percent / BF3*OEt2 / tetrahydrofuran; hexane; diethyl ether / 24 h / -78 °C
With
2,6-dimethylpyridine; n-butyllithium; potassium tert-butylate; hydrogen; sodium hydride; diisobutylaluminium hydride;
Ru2Cl4-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt3;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
5.3: Brown asymmetric crotylation;
DOI:10.1021/jo0503862
