Technology Process of (6ξ,8ξ)-6,9-anhydro-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-C-methyl-D-glycero-D-threo-4,7-decodiulose
There total 18 articles about (6ξ,8ξ)-6,9-anhydro-1,3-O-benzylidene-8-<(benzyloxy)methyl>-2,5,8,10-tetradeoxy-2-C-methyl-D-glycero-D-threo-4,7-decodiulose 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:
-
With
oxalyl dichloride; N,N-dimethyl-formamide;
In
dichloromethane;
at -78 ℃;
for 0.316667h;
DOI:10.1021/jo00385a024
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 97.3 percent / pyridine, N',N'-dimethylaminopyridine / CH2Cl2 / 24 h
2: 90 percent / H2 / 10percent Pd/C / ethanol / 18 h / 2585.7 Torr
3: oxalyl chloride, DMSO / CH2Cl2 / 0.43 h / -78 °C
4: pyridine / benzene / 0.33 h / 5 °C
5: 90.5 percent / N-methoxymorpholine N-oxide, OsO4 / acetone; H2O; 2-methyl-propan-2-ol / 10.5 h
6: oxalyl chloride, DMSO / CH2Cl2 / -78 - 30 °C
7: CH2Cl2 / 1.33 h / -30 - 0 °C
8: 71.4 percent / LiBF4, p-toluenesulfonic acid / acetone; CH2Cl2 / 12 h
9: LiAlH4 / tetrahydrofuran / 4 h / -78 - 25 °C
10: 56.2 percent / p-toluenesulfonic acid / benzene / 22 h
11: 81.3 percent / oxalyl chloride, DMF / CH2Cl2 / 0.32 h / -78 °C
With
pyridine; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium tetrafluoroborate; oxalyl dichloride; N',N'-dimethylaminopyridine; N-methoxymorpholine N-oxide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/jo00385a024
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 90 percent / H2 / 10percent Pd/C / ethanol / 18 h / 2585.7 Torr
2: oxalyl chloride, DMSO / CH2Cl2 / 0.43 h / -78 °C
3: pyridine / benzene / 0.33 h / 5 °C
4: 90.5 percent / N-methoxymorpholine N-oxide, OsO4 / acetone; H2O; 2-methyl-propan-2-ol / 10.5 h
5: oxalyl chloride, DMSO / CH2Cl2 / -78 - 30 °C
6: CH2Cl2 / 1.33 h / -30 - 0 °C
7: 71.4 percent / LiBF4, p-toluenesulfonic acid / acetone; CH2Cl2 / 12 h
8: LiAlH4 / tetrahydrofuran / 4 h / -78 - 25 °C
9: 56.2 percent / p-toluenesulfonic acid / benzene / 22 h
10: 81.3 percent / oxalyl chloride, DMF / CH2Cl2 / 0.32 h / -78 °C
With
pyridine; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium tetrafluoroborate; oxalyl dichloride; N-methoxymorpholine N-oxide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/jo00385a024
