Technology Process of 1-adamantanyl-3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranoside
There total 8 articles about 1-adamantanyl-3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranoside 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:
-
1,2,3-trimethoxybenzene; 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (S)-S-oxide;
With
2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride;
In
dichloromethane;
at -60 - -10 ℃;
for 0.166667h;
Inert atmosphere;
Molecular sieve;
1-adamanthanol;
In
dichloromethane;
at -10 - 20 ℃;
for 24h;
optical yield given as %de;
diastereoselective reaction;
Inert atmosphere;
Molecular sieve;
DOI:10.1002/chem.201101889
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: toluene-4-sulfonic acid / Inert atmosphere
2.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / Inert atmosphere
3.1: pyridine / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.42 h / -78 °C / Inert atmosphere
5.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.17 h / -60 - -10 °C / Inert atmosphere; Molecular sieve
5.2: 24 h / -10 - 20 °C / Inert atmosphere; Molecular sieve
With
pyridine; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid;
In
dichloromethane; 1,2-dichloro-ethane;
DOI:10.1002/chem.201101889
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: sodium methylate / methanol / Inert atmosphere
2.1: toluene-4-sulfonic acid / Inert atmosphere
3.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / Inert atmosphere
4.1: pyridine / Inert atmosphere
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.42 h / -78 °C / Inert atmosphere
6.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.17 h / -60 - -10 °C / Inert atmosphere; Molecular sieve
6.2: 24 h / -10 - 20 °C / Inert atmosphere; Molecular sieve
With
pyridine; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid;
In
methanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1002/chem.201101889
