Technology Process of (1R,2R,4S,5R,6S,8R)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-11-methylene-12-oxa-tricyclo[6.3.1.01,6]dodecan-4-ol
There total 10 articles about (1R,2R,4S,5R,6S,8R)-5-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-11-methylene-12-oxa-tricyclo[6.3.1.01,6]dodecan-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:
-
Acetic acid (1R,2R,4S,5R,6S,8S)-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-11-oxo-12-oxa-tricyclo[6.3.1.01,6]dodec-9-en-4-yl ester;
With
hydrogen;
palladium on activated charcoal;
In
ethyl acetate;
under 2534.03 Torr;
Methylenetriphenylphosphorane;
In
tetrahydrofuran;
Heating;
DOI:10.1021/ja972279y
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: LDA / -78 °C
2.1: n-BuLi / tetrahydrofuran / -78 °C
2.2: 98 percent / tetrahydrofuran
3.1: 97 percent / pyridine / CH2Cl2 / 0 °C
4.1: 100 percent / NaBH4 / methanol / 0 °C
5.1: 100 percent / m-chloroperoxybenzoic acid / tetrahydrofuran / 0 °C
6.1: 96 percent / DMAP; pyridine
7.1: 84 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 80 °C
8.1: H2 / Pd/C / ethyl acetate / 2534.03 Torr
8.2: tetrahydrofuran / Heating
With
pyridine; dmap; sodium tetrahydroborate; n-butyllithium; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile;
1.1: Metallation / 1.2: Methylation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation / 4.1: Reduction / 5.1: Oxidation / 6.1: Acetylation / 7.1: Cycloaddition / 8.1: Hydrogenation / 8.2: Wittig olefination;
DOI:10.1021/ja972279y
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: BF3*OEt2 / tetrahydrofuran / -78 °C
2.1: TsOH / CH2Cl2
3.1: LDA / -78 °C
4.1: n-BuLi / tetrahydrofuran / -78 °C
4.2: 98 percent / tetrahydrofuran
5.1: 97 percent / pyridine / CH2Cl2 / 0 °C
6.1: 100 percent / NaBH4 / methanol / 0 °C
7.1: 100 percent / m-chloroperoxybenzoic acid / tetrahydrofuran / 0 °C
8.1: 96 percent / DMAP; pyridine
9.1: 84 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 80 °C
10.1: H2 / Pd/C / ethyl acetate / 2534.03 Torr
10.2: tetrahydrofuran / Heating
With
pyridine; dmap; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile;
1.1: Ring cleavage / 2.1: Cyclization / 3.1: Metallation / 3.2: Methylation / 4.1: Metallation / 4.2: Addition / 5.1: Acetylation / 6.1: Reduction / 7.1: Oxidation / 8.1: Acetylation / 9.1: Cycloaddition / 10.1: Hydrogenation / 10.2: Wittig olefination;
DOI:10.1021/ja972279y
