Technology Process of (5S,5aS,8aR,9R)-5-(Dimethyl-phenyl-silanyl)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester
There total 6 articles about (5S,5aS,8aR,9R)-5-(Dimethyl-phenyl-silanyl)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester 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:
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620116-56-5
(5S,5aS,8aR,9R)-5-(Dimethyl-phenyl-silanyl)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester
- Guidance literature:
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With
2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane;
In
benzene;
at 80 ℃;
for 14h;
DOI:10.1021/ja0376588
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620116-56-5
(5S,5aS,8aR,9R)-5-(Dimethyl-phenyl-silanyl)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester
- Guidance literature:
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Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 3 h / -78 °C
1.2: tetrahydrofuran / -78 - 25 °C
1.3: 202.6 mg / aq. KHCO3; aq. K2CO3 / methanol / 55 h / 25 °C
2.1: MeOTf / CH2Cl2 / 2 h / 25 °C
2.2: NaBH4 / tetrahydrofuran; methanol / 0.5 h / 25 °C
2.3: 100 percent / (CO2H)2*H2O / tetrahydrofuran; H2O / 16 h / 25 °C
3.1: 79 percent / Bu3SnH; SiO2 / toluene / 10 h / 80 °C
4.1: 99 percent / pyridine / CH2Cl2 / 2 h / 25 °C
5.1: 40 percent / tris(trimethylsilyl)silane; AIBN / benzene / 14 h / 80 °C
With
pyridine; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; tri-n-butyl-tin hydride; silica gel; methyl trifluoromethanesulfonate;
In
tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1021/ja0376588
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-
620116-56-5
(5S,5aS,8aR,9R)-5-(Dimethyl-phenyl-silanyl)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 3 h / -78 °C
1.2: tetrahydrofuran / -78 - 25 °C
1.3: 202.6 mg / aq. KHCO3; aq. K2CO3 / methanol / 55 h / 25 °C
2.1: MeOTf / CH2Cl2 / 2 h / 25 °C
2.2: NaBH4 / tetrahydrofuran; methanol / 0.5 h / 25 °C
2.3: 100 percent / (CO2H)2*H2O / tetrahydrofuran; H2O / 16 h / 25 °C
3.1: 79 percent / Bu3SnH; SiO2 / toluene / 10 h / 80 °C
4.1: 99 percent / pyridine / CH2Cl2 / 2 h / 25 °C
5.1: 40 percent / tris(trimethylsilyl)silane; AIBN / benzene / 14 h / 80 °C
With
pyridine; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; tri-n-butyl-tin hydride; silica gel; methyl trifluoromethanesulfonate;
In
tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1021/ja0376588