Technology Process of (2R,3R,4R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-en-1-one
There total 4 articles about (2R,3R,4R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-en-1-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one;
With
titanium tetrachloride;
In
dichloromethane;
for 0.25h;
Cooling with ice;
With
N-ethyl-N,N-diisopropylamine;
In
1-methyl-pyrrolidin-2-one; dichloromethane;
at -78 - 0 ℃;
for 0.75h;
(R)-2-((4-methoxybenzyl)oxy)-4-methylpent-4-enal;
In
1-methyl-pyrrolidin-2-one; dichloromethane;
at -78 - -20 ℃;
for 13h;
Overall yield = 81 %; Overall yield = 3.41 g;
DOI:10.1021/ol5008422
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / water; tetrahydrofuran / 2 h / 0 °C
2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.42 h / -78 - 0 °C / Inert atmosphere
3.1: titanium tetrachloride / dichloromethane / 0.25 h / Cooling with ice
3.2: 0.75 h / -78 - 0 °C
3.3: 13 h / -78 - -20 °C
With
sodium tetrahydroborate; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; dichloromethane; water;
2.1: |Swern Oxidation / 3.1: |Aldol Condensation / 3.2: |Aldol Condensation / 3.3: |Aldol Condensation;
DOI:10.1021/ol5008422
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.42 h / -78 - 0 °C / Inert atmosphere
2.1: titanium tetrachloride / dichloromethane / 0.25 h / Cooling with ice
2.2: 0.75 h / -78 - 0 °C
2.3: 13 h / -78 - -20 °C
With
oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
1.1: |Swern Oxidation / 2.1: |Aldol Condensation / 2.2: |Aldol Condensation / 2.3: |Aldol Condensation;
DOI:10.1021/ol5008422
