Technology Process of (5aR,8aR,9R)-5,8-Dioxo-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 7 articles about (5aR,8aR,9R)-5,8-Dioxo-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:
-
-
(5aR,8aR,9R)-5-Hydroxy-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
-
-
620116-57-6
(5aR,8aR,9R)-5,8-Dioxo-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:
-
With
Dess-Martin periodane;
In
dichloromethane;
at 25 ℃;
for 0.5h;
DOI:10.1021/ja0376588
-
-
620116-57-6
(5aR,8aR,9R)-5,8-Dioxo-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 7 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
6.1: BF3*2AcOH / CH2Cl2 / 27 h / 50 °C
6.2: m-CPBA; KF / dimethylformamide / 1 h / 25 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C
With
pyridine; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; tri-n-butyl-tin hydride; boron trifluoride diacetate; silica gel; Dess-Martin periodane; methyl trifluoromethanesulfonate;
In
tetrahydrofuran; dichloromethane; toluene; benzene;
6.2: Fleming-Tamao oxidation;
DOI:10.1021/ja0376588
-
-
620116-57-6
(5aR,8aR,9R)-5,8-Dioxo-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: 79 percent / Bu3SnH; SiO2 / toluene / 10 h / 80 °C
2.1: 99 percent / pyridine / CH2Cl2 / 2 h / 25 °C
3.1: 40 percent / tris(trimethylsilyl)silane; AIBN / benzene / 14 h / 80 °C
4.1: BF3*2AcOH / CH2Cl2 / 27 h / 50 °C
4.2: m-CPBA; KF / dimethylformamide / 1 h / 25 °C
5.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C
With
pyridine; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; tri-n-butyl-tin hydride; boron trifluoride diacetate; silica gel; Dess-Martin periodane;
In
dichloromethane; toluene; benzene;
4.2: Fleming-Tamao oxidation;
DOI:10.1021/ja0376588