Technology Process of (2R,3R)-2-[(E)-(1S,2R,5S,6S,8S,9R)-2-Benzyloxy-8,10-bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-1,5,9-trimethyl-dec-3-enyl]-5-methoxy-3-methyl-tetrahydro-furan
There total 22 articles about (2R,3R)-2-[(E)-(1S,2R,5S,6S,8S,9R)-2-Benzyloxy-8,10-bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-1,5,9-trimethyl-dec-3-enyl]-5-methoxy-3-methyl-tetrahydro-furan 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:
-
(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde; [(2R,3S,5S,6R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-2,6-dimethyl-heptane-1-sulfonyl]-benzene;
With
n-butyllithium;
In
tetrahydrofuran;
at -78 ℃;
With
sodium dihydrogenphosphate; sodium amalgam;
In
methanol;
at 0 ℃;
Further stages.;
DOI:10.1016/j.tetlet.2004.05.078
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 8.15 g / imidazole / dimethylformamide / 11 h / 50 °C
2.1: 92 percent / H2; NaHCO3 / Pd/C / ethyl acetate / 11 h / 20 °C
3.1: 89 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
4.1: dibutylboron triflate; Et3N / CH2Cl2 / 0.67 h / 0 °C
4.2: 100 percent / CH2Cl2 / 2.33 h / -78 - 0 °C
5.1: 100 percent / LiBH4; EtOH / 0.5 h / -10 °C
6.1: 99 percent / tributylphosphine / dimethylformamide / 11 h / 20 °C
7.1: 99 percent / m-chloroperoxybenzoic acid; NaHCO3 / CH2Cl2 / 0.33 h / 0 - 20 °C
8.1: 95 percent / NaH / tetrahydrofuran / 16 h / 20 °C
9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
9.2: 67 percent / tetrahydrofuran; hexane / -78 °C
10.1: 196 mg / sodium amalgam; Na2HPO4 / methanol / 2 h / 0 °C
With
1H-imidazole; disodium hydrogenphosphate; sodium amalgam; lithium borohydride; n-butyllithium; oxalyl dichloride; ethanol; tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
9.2: Julia coupling;
DOI:10.1016/j.tet.2006.06.046
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 92 percent / H2; NaHCO3 / Pd/C / ethyl acetate / 11 h / 20 °C
2.1: 89 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
3.1: dibutylboron triflate; Et3N / CH2Cl2 / 0.67 h / 0 °C
3.2: 100 percent / CH2Cl2 / 2.33 h / -78 - 0 °C
4.1: 100 percent / LiBH4; EtOH / 0.5 h / -10 °C
5.1: 99 percent / tributylphosphine / dimethylformamide / 11 h / 20 °C
6.1: 99 percent / m-chloroperoxybenzoic acid; NaHCO3 / CH2Cl2 / 0.33 h / 0 - 20 °C
7.1: 95 percent / NaH / tetrahydrofuran / 16 h / 20 °C
8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
8.2: 67 percent / tetrahydrofuran; hexane / -78 °C
9.1: 196 mg / sodium amalgam; Na2HPO4 / methanol / 2 h / 0 °C
With
disodium hydrogenphosphate; sodium amalgam; lithium borohydride; n-butyllithium; oxalyl dichloride; ethanol; tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
8.2: Julia coupling;
DOI:10.1016/j.tet.2006.06.046
