Technology Process of (2R,3S,9S,12S,13S)-15-Benzyloxy-3-chloro-2-(3,4-dimethoxy-benzyloxy)-13-(4-methoxy-benzyloxy)-1-methoxymethoxy-9-methyl-12-triethylsilanyloxy-pentadec-5-yne-4,10-diol
There total 12 articles about (2R,3S,9S,12S,13S)-15-Benzyloxy-3-chloro-2-(3,4-dimethoxy-benzyloxy)-13-(4-methoxy-benzyloxy)-1-methoxymethoxy-9-methyl-12-triethylsilanyloxy-pentadec-5-yne-4,10-diol 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:
-
(5S,8S,9S)-11-Benzyloxy-9-(4-methoxy-benzyloxy)-5-methyl-8-triethylsilanyloxy-undec-1-yn-6-ol;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 1h;
(2R,3R)-2-chloro-3-(3,4-dimethoxybenzyloxy)-4-(methoxymethoxy)butanal;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 0.5h;
DOI:10.1021/ol0609457
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 87 percent / titanium tetraisopropoxide; (-)-D-diisopropyl tartrate; t-butylhydroperoxide / molecular sieves 4 Angstroem / CH2Cl2; decane / 16 h / -20 °C
2.1: 822 mg / trimethyl borate; LiCl; acetic acid / acetone / 12 h
3.1: 1.24 g / imidazole / CH2Cl2 / 12 h / 0 - 20 °C
4.1: 676 mg / BF3*Et2O / CH2Cl2 / 1 h / 0 °C
5.1: 415 mg / p-toluenesulfonic acid monohydrate; tetrabutylammonium fluoride / tetrahydrofuran / 3 h
6.1: 98 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 1 h
7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
7.2: 48 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; (-)-diisopropyl tartrate; Trimethyl borate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; lithium chloride;
4 A molecular sieve;
In
tetrahydrofuran; decane; hexane; dichloromethane; acetone;
1.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol0609457
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 1.24 g / imidazole / CH2Cl2 / 12 h / 0 - 20 °C
2.1: 676 mg / BF3*Et2O / CH2Cl2 / 1 h / 0 °C
3.1: 415 mg / p-toluenesulfonic acid monohydrate; tetrabutylammonium fluoride / tetrahydrofuran / 3 h
4.1: 98 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 1 h
5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
5.2: 48 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
With
1H-imidazole; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid;
In
tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0609457
