Technology Process of (R)-2-((4S,5S,6R)-6-{(R)-1-Benzyloxy-2-[(2R,4R,5R)-4-((1R,2S,3S,4R)-2-benzyloxy-4-hydroxy-1,3-dimethyl-hexyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-1-methyl-ethyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid
There total 7 articles about (R)-2-((4S,5S,6R)-6-{(R)-1-Benzyloxy-2-[(2R,4R,5R)-4-((1R,2S,3S,4R)-2-benzyloxy-4-hydroxy-1,3-dimethyl-hexyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-1-methyl-ethyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid which
guide to synthetic route it.
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synthetic route:
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123219-52-3
(R)-2-((4S,5S,6R)-6-{(R)-1-Benzyloxy-2-[(2R,4R,5R)-4-((1R,2S,3S,4R)-2-benzyloxy-4-hydroxy-1,3-dimethyl-hexyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-1-methyl-ethyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid
- Guidance literature:
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Multi-step reaction with 4 steps
1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 0.25 h / 20 °C
2: n-Bu4NF / tetrahydrofuran / 3 h / 40 °C
3: 1) ozone, 2) dimethyl sulfide / CH2Cl2 / 1) -78 deg C, 2) room temperature, 1 h
4: m-chloroperbenzoic acid / tetrahydrofuran; H2O / 0.5 h / 20 °C / phosphate buffer (pH: 7.0)
With
dimethylsulfide; tetrabutyl ammonium fluoride; ozone; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane; water;
DOI:10.1007/BF00953721
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123219-52-3
(R)-2-((4S,5S,6R)-6-{(R)-1-Benzyloxy-2-[(2R,4R,5R)-4-((1R,2S,3S,4R)-2-benzyloxy-4-hydroxy-1,3-dimethyl-hexyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-1-methyl-ethyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid
- Guidance literature:
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Multi-step reaction with 6 steps
1: 64.2 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C / 1) 30 min, 2) 15 min
2: LiAlH4 / diethyl ether / 0.17 h
3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 0.25 h / 20 °C
4: n-Bu4NF / tetrahydrofuran / 3 h / 40 °C
5: 1) ozone, 2) dimethyl sulfide / CH2Cl2 / 1) -78 deg C, 2) room temperature, 1 h
6: m-chloroperbenzoic acid / tetrahydrofuran; H2O / 0.5 h / 20 °C / phosphate buffer (pH: 7.0)
With
lithium aluminium tetrahydride; dimethylsulfide; tetrabutyl ammonium fluoride; ozone; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1007/BF00953721
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123219-52-3
(R)-2-((4S,5S,6R)-6-{(R)-1-Benzyloxy-2-[(2R,4R,5R)-4-((1R,2S,3S,4R)-2-benzyloxy-4-hydroxy-1,3-dimethyl-hexyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-1-methyl-ethyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionic acid
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 64.2 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C / 1) 30 min, 2) 15 min
2: LiAlH4 / diethyl ether / 0.17 h
3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 0.25 h / 20 °C
4: n-Bu4NF / tetrahydrofuran / 3 h / 40 °C
5: 1) ozone, 2) dimethyl sulfide / CH2Cl2 / 1) -78 deg C, 2) room temperature, 1 h
6: m-chloroperbenzoic acid / tetrahydrofuran; H2O / 0.5 h / 20 °C / phosphate buffer (pH: 7.0)
With
lithium aluminium tetrahydride; dimethylsulfide; tetrabutyl ammonium fluoride; ozone; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1007/BF00953721