Technology Process of (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[3-fluoro-4-(1,1,2,2,2-pentadeuterioethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde
There total 13 articles about (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[3-fluoro-4-(1,1,2,2,2-pentadeuterioethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde which
guide to synthetic route it.
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synthetic route:
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1358581-59-5
[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[3-fluoro-4-(1,1,2,2,2-pentadeuterioethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol
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1358581-62-0
(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[3-fluoro-4-(1,1,2,2,2-pentadeuterioethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde
- Guidance literature:
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[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[3-fluoro-4-(1,1,2,2,2-pentadeuterioethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol;
With
oxalyl dichloride;
In
dichloromethane; dimethyl sulfoxide;
for 0.75h;
With
triethylamine;
In
dichloromethane; dimethyl sulfoxide;
at 20 ℃;
for 2.5h;
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1358581-62-0
(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[3-fluoro-4-(1,1,2,2,2-pentadeuterioethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: potassium carbonate / acetone / 5 h / Reflux
2.1: aluminum (III) chloride / dichloromethane / 16 h / 0 °C
3.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h / 20 °C
4.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 3 h
5.1: boron tribromide / dichloromethane / 4 h / Cooling with ice
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h
6.2: 18 h
7.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C
7.2: 3 h / -78 °C
7.3: 16 h / 20 °C
8.1: pyridine; dmap / 24 h
9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C
9.2: 3 h
10.1: acetyl chloride; methanol / 4 h
11.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h
11.2: 2.5 h / 20 °C
With
pyridine; methanol; triethylsilane; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; boron tribromide; sodium hydride; potassium carbonate; acetyl chloride; triphenylphosphine;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; mineral oil;
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1358581-62-0
(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[3-fluoro-4-(1,1,2,2,2-pentadeuterioethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: aluminum (III) chloride / dichloromethane / 16 h / 0 °C
2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h / 20 °C
3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 3 h
4.1: boron tribromide / dichloromethane / 4 h / Cooling with ice
5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h
5.2: 18 h
6.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C
6.2: 3 h / -78 °C
6.3: 16 h / 20 °C
7.1: pyridine; dmap / 24 h
8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C
8.2: 3 h
9.1: acetyl chloride; methanol / 4 h
10.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h
10.2: 2.5 h / 20 °C
With
pyridine; methanol; triethylsilane; dmap; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; boron tribromide; sodium hydride; acetyl chloride; triphenylphosphine;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;