Technology Process of (1S,2S,3S,4S,6S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methyl-6-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carbaldehyde
There total 9 articles about (1S,2S,3S,4S,6S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methyl-6-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carbaldehyde 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:
-
Multi-step reaction with 9 steps
1: N-chlorosuccinimide / CCl4 / 3 h / 25 °C
2: potassium tert-butoxide / tetrahydrofuran / 4.5 h / 25 °C
3: 1.) sec-butyllithium / 1.) DME, cyclohexane, from -78 deg C to -40 deg C, 15 min, 2.) from -78 deg C to 0 deg C
4: d-camphorsulfonic acid / methanol / 2 h / 25 °C
5: CHCl3 / 12 h / 25 °C
6: H2 / 5percent Pd/C / ethyl acetate / 2.5 h / 2844.3 Torr
7: 75 percent / LiAlH4 / tetrahydrofuran / 20 h / 40 °C
8: 1.) NaH / 1.) THF
9: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min, 2a.) -60 deg C, 5 min, 2b.) from -60 deg C to 25 deg C
With
N-chloro-succinimide; lithium aluminium tetrahydride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; sec.-butyllithium; sodium hydride; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; tetrachloromethane; chloroform; ethyl acetate;
DOI:10.1021/jo00262a024
- Guidance literature:
-
Multi-step reaction with 8 steps
1: potassium tert-butoxide / tetrahydrofuran / 4.5 h / 25 °C
2: 1.) sec-butyllithium / 1.) DME, cyclohexane, from -78 deg C to -40 deg C, 15 min, 2.) from -78 deg C to 0 deg C
3: d-camphorsulfonic acid / methanol / 2 h / 25 °C
4: CHCl3 / 12 h / 25 °C
5: H2 / 5percent Pd/C / ethyl acetate / 2.5 h / 2844.3 Torr
6: 75 percent / LiAlH4 / tetrahydrofuran / 20 h / 40 °C
7: 1.) NaH / 1.) THF
8: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min, 2a.) -60 deg C, 5 min, 2b.) from -60 deg C to 25 deg C
With
lithium aluminium tetrahydride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; sec.-butyllithium; sodium hydride; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; chloroform; ethyl acetate;
DOI:10.1021/jo00262a024
- Guidance literature:
-
Multi-step reaction with 6 steps
1: d-camphorsulfonic acid / methanol / 2 h / 25 °C
2: CHCl3 / 12 h / 25 °C
3: H2 / 5percent Pd/C / ethyl acetate / 2.5 h / 2844.3 Torr
4: 75 percent / LiAlH4 / tetrahydrofuran / 20 h / 40 °C
5: 1.) NaH / 1.) THF
6: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min, 2a.) -60 deg C, 5 min, 2b.) from -60 deg C to 25 deg C
With
lithium aluminium tetrahydride; oxalyl dichloride; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; chloroform; ethyl acetate;
DOI:10.1021/jo00262a024
