Technology Process of (4S)-[(1R,2S,3S,4S)-1,2,4-tris(benzyloxy)-3-[(2-trimethylsilylethoxy)methoxy]-6-(tert-butyldiphenylsilyloxy)hexyl]-2,2-dimethyl-1,3-dioxolane
There total 9 articles about (4S)-[(1R,2S,3S,4S)-1,2,4-tris(benzyloxy)-3-[(2-trimethylsilylethoxy)methoxy]-6-(tert-butyldiphenylsilyloxy)hexyl]-2,2-dimethyl-1,3-dioxolane 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
tetra-(n-butyl)ammonium iodide; sodium hydride;
In
tetrahydrofuran;
at 0 - 40 ℃;
DOI:10.1021/ol062570v
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: Chx2BCl; triethylamine / diethyl ether / 1 h / 0 °C
1.2: diethyl ether / 5 h / 0 °C
1.3: 72 percent / phosphate buffer; H2O2 / diethyl ether; methanol; H2O / 1 h / 20 °C / pH 7
2.1: 75 percent / 4-(dimethylamino)pyridine; i-Pr2NEt / CH2Cl2 / 24 h / 20 °C
3.1: 80 percent / LiBH4 / diethyl ether / 2 h / -90 °C
4.1: 82 percent Turnov. / DDQ / tetrahydrofuran; H2O / 24 h / 20 °C
5.1: 80 percent / NaH; TBAI / tetrahydrofuran / 0 - 40 °C
With
dmap; lithium borohydride; dicyclohexylboron chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; dichloromethane; water;
1.2: aldol addition;
DOI:10.1021/ol062570v
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
2.1: Chx2BCl; triethylamine / diethyl ether / 1 h / 0 °C
2.2: diethyl ether / 5 h / 0 °C
2.3: 72 percent / phosphate buffer; H2O2 / diethyl ether; methanol; H2O / 1 h / 20 °C / pH 7
3.1: 75 percent / 4-(dimethylamino)pyridine; i-Pr2NEt / CH2Cl2 / 24 h / 20 °C
4.1: 80 percent / LiBH4 / diethyl ether / 2 h / -90 °C
5.1: 82 percent Turnov. / DDQ / tetrahydrofuran; H2O / 24 h / 20 °C
6.1: 80 percent / NaH; TBAI / tetrahydrofuran / 0 - 40 °C
With
dmap; lithium borohydride; oxalyl dichloride; dicyclohexylboron chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; dichloromethane; water;
1.1: Swern oxidation / 2.2: aldol addition;
DOI:10.1021/ol062570v
![(1S,2S,3R,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(2-trimethylsilylethoxy)methoxy]hexane-1,2-diol](/Databaselist/images/loading.webp)
