Technology Process of (R)-3-((2R,3S,4S,5S,6S,8R)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoyl)-4-benzyloxazolidin-2-one
There total 6 articles about (R)-3-((2R,3S,4S,5S,6S,8R)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-(triisopropylsilyloxy)nonanoyl)-4-benzyloxazolidin-2-one 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:
-
(3R)-3-propionyl-4-benzyloxazolidin-2-one;
With
di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 0 ℃;
for 1h;
(3S,4S,6R)-3-(4-methoxybenzyloxy)-2,4,6,-trimethyl-7-(triisopropylsilyloxy)heptanal;
In
dichloromethane;
at -78 - -20 ℃;
for 4h;
DOI:10.1021/jo062047u
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: Bu2BOTf; i-Pr2NEt / CH2Cl2 / 1 h / 0 °C
1.2: 78 percent / CH2Cl2 / 2.5 h / -78 - -10 °C
2.1: 88 percent / LiBH4 / tetrahydrofuran; methanol / 0.75 h / 0 °C
3.1: 92 percent / CSA / CH2Cl2 / 12 h / 20 °C
4.1: 94 percent / DIBAL-H / toluene / 1 h / 0 °C
5.1: 86 percent / (COCl)2; DMSO; i-Pr2NEt / CH2Cl2 / -78 - 0 °C
6.1: Bu2BOTf; i-Pr2NEt / CH2Cl2 / 1 h / 0 °C
6.2: 76 percent / CH2Cl2 / 4 h / -78 - -20 °C
With
lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
1.2: Evans Aldol Reaction / 5.1: Swern Oxidation / 6.2: Evans Aldol Reaction;
DOI:10.1021/jo062047u
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 92 percent / CSA / CH2Cl2 / 12 h / 20 °C
2.1: 94 percent / DIBAL-H / toluene / 1 h / 0 °C
3.1: 86 percent / (COCl)2; DMSO; i-Pr2NEt / CH2Cl2 / -78 - 0 °C
4.1: Bu2BOTf; i-Pr2NEt / CH2Cl2 / 1 h / 0 °C
4.2: 76 percent / CH2Cl2 / 4 h / -78 - -20 °C
With
oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
dichloromethane; toluene;
3.1: Swern Oxidation / 4.2: Evans Aldol Reaction;
DOI:10.1021/jo062047u
