(5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

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Chemical Name:(5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
CAS No.:342824-63-9
Molecular Formula:C₂₇H₂₃FN₂O₉
Molecular Weight:538.486
Hs Code.:

Synonyms:(5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

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Chemical Property of (5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

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Technology Process of (5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

There total 5 articles about (5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 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:

Reference yield: 70.0%

: 100-01-6,104810-17-5
4-nitro-aniline

: (5R,5aS,8aR,9S)-5a-Fluoro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

: 342824-63-9
(5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Guidance literature:: (5R,5aS,8aR,9S)-5a-Fluoro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one; With hydrogen bromide; In diethyl ether; 1,2-dichloro-ethane; at 0 ℃; for 2h;

4-nitro-aniline; With barium carbonate; In tetrahydrofuran; at 20 ℃; Further stages.;
DOI:10.1021/jm000377f

Reference yield:

: 112711-16-7
(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

: 342824-63-9
(5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaHMDS / tetrahydrofuran

1.2: 99 percent / NFSi / tetrahydrofuran / -78 °C

2.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran

3.1: CH₂Cl₂ / 6 h / 0 °C

3.2: 80 percent / BaCO₃ / acetone; H₂O / 1 h / 40 °C

4.1: HBr(g) / 1,2-dichloro-ethane; diethyl ether / 2 h / 0 °C

4.2: 70 percent / BaCO₃ / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; hydrogen bromide; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; 1.1: Davis-Differding reaction;
DOI:10.1021/jm000377f

Reference yield:

: 223777-99-9
9-(tert-butyl-dimethyl-silanyloxy)-5a-fluoro-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

: 342824-63-9
(5R,5aS,8aS,9S)-5a-Fluoro-5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-(4-nitro-phenylamino)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran

2.1: CH₂Cl₂ / 6 h / 0 °C

2.2: 80 percent / BaCO₃ / acetone; H₂O / 1 h / 40 °C

3.1: HBr(g) / 1,2-dichloro-ethane; diethyl ether / 2 h / 0 °C

3.2: 70 percent / BaCO₃ / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; hydrogen bromide; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jm000377f