Technology Process of methyl 2,3-di-O-benzyl-4,7,8-trideoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-D-glycero-α-D-galacto-octa-7-enopyranoside
There total 8 articles about methyl 2,3-di-O-benzyl-4,7,8-trideoxy-4-C-[(1R)-1-triethylsilyloxyallyl]-D-glycero-α-D-galacto-octa-7-enopyranoside 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 8 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
2.2: 12 h / 0 - 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 - 0 °C / Inert atmosphere
4.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
5.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 60 °C
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / Cooling with ice
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
7.2: 0.5 h / -78 - 0 °C / Inert atmosphere
8.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
With
1H-imidazole; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
1.1: |Wittig Olefination / 3.1: |Swern Oxidation / 4.1: |Grignard Reaction / 7.1: |Swern Oxidation / 8.1: |Grignard Reaction;
DOI:10.1002/ejoc.201400028
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
1.2: 0.5 h / -78 - 0 °C / Inert atmosphere
2.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
3.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 60 °C
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / Cooling with ice
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
5.2: 0.5 h / -78 - 0 °C / Inert atmosphere
6.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
With
1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
1.1: |Swern Oxidation / 2.1: |Grignard Reaction / 5.1: |Swern Oxidation / 6.1: |Grignard Reaction;
DOI:10.1002/ejoc.201400028
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
1.2: 12 h / 0 - 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 - 0 °C / Inert atmosphere
3.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
4.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 60 °C
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / Cooling with ice
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
6.2: 0.5 h / -78 - 0 °C / Inert atmosphere
7.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
With
1H-imidazole; oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
2.1: |Swern Oxidation / 3.1: |Grignard Reaction / 6.1: |Swern Oxidation / 7.1: |Grignard Reaction;
DOI:10.1002/ejoc.201400028
