N-(2-(3-hydroxy-5-methoxy-3,3a,3a¹,9a-tetrahydrophenanthro[4,5-bcd]furan-3a¹-yl)ethyl)-N,4-dimethylbenzenesulfonamide

Base Information

• Chemical Name: N-(2-(3-hydroxy-5-methoxy-3,3a,3a¹,9a-tetrahydrophenanthro[4,5-bcd]furan-3a¹-yl)ethyl)-N,4-dimethylbenzenesulfonamide
• CAS No.: 1440947-69-2
• Molecular Formula: C₂₅H₂₇NO₅S
• Molecular Weight: 453.559

Synonyms:

Chemical Property of N-(2-(3-hydroxy-5-methoxy-3,3a,3a¹,9a-tetrahydrophenanthro[4,5-bcd]furan-3a¹-yl)ethyl)-N,4-dimethylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2-(3-hydroxy-5-methoxy-3,3a,3a¹,9a-tetrahydrophenanthro[4,5-bcd]furan-3a¹-yl)ethyl)-N,4-dimethylbenzenesulfonamide

There total 36 articles about N-(2-(3-hydroxy-5-methoxy-3,3a,3a¹,9a-tetrahydrophenanthro[4,5-bcd]furan-3a¹-yl)ethyl)-N,4-dimethylbenzenesulfonamide 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:

p-toluenesulfonyl chloride (98-59-9) + 5-methoxy-9b-(2-methylaminoethyl)-3,3a,9a,9b-tetrahydrophenanthro[4,5-bcd]furan-3-ol (481634-93-9) → N-(2-(3-hydroxy-5-methoxy-3,3a,3a1,9a-tetrahydrophenanthro[4,5-bcd]furan-3a1-yl)ethyl)-N,4-dimethylbenzenesulfonamide (1440947-69-2)

Guidance literature:

With pyridine; dmap; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1002/chem.201203284

Reference yield:

(2S,3R)-3-((tert-butyldimethylsilyl)oxy)-5-hydroxy-2-((4-methoxybenzyl)oxy)cyclohexanone → N-(2-(3-hydroxy-5-methoxy-3,3a,3a1,9a-tetrahydrophenanthro[4,5-bcd]furan-3a1-yl)ethyl)-N,4-dimethylbenzenesulfonamide (1440947-69-2)

Guidance literature:

Multi-step reaction with 16 steps

1.1: methanesulfonyl chloride; dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2.1: L-Selectride / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

2.2: 0.33 h / -78 - 20 °C / Inert atmosphere

3.1: triphenylphosphine; sodium carbonate; palladium diacetate / water; 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

3.2: 3.5 h / 20 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.75 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

6.1: 2-hydroxynitrobenzene / 91 h / 140 - 170 °C / Inert atmosphere; Sealed tube

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h / 60 °C / Inert atmosphere

9.1: silver trifluoromethanesulfonate; Phenylselenyl chloride; boron trifluoride diethyl etherate / ethyl acetate / 1 h / 0 - 20 °C / Inert atmosphere

9.2: 1.5 h / 0 - 20 °C / Inert atmosphere

10.1: methanol; cerium(III) chloride heptahydrate / 0.5 h / 0 - 20 °C / Inert atmosphere

10.2: 0.33 h / 0 °C / Inert atmosphere

11.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

12.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

13.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

13.2: 0.25 h / -78 °C / Inert atmosphere

14.1: toluene-4-sulfonic acid / 1,2-dichloro-ethane / 15 h / 20 °C / Inert atmosphere

15.1: methanol; water / 0.17 h / 20 °C / Inert atmosphere

15.2: 0.25 h / 0 - 20 °C / Inert atmosphere

16.1: dmap; pyridine / 3 h / 80 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; methanol; dmap; lithium aluminium tetrahydride; Phenylselenyl chloride; oxalyl dichloride; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; palladium diacetate; L-Selectride; sodium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2-hydroxynitrobenzene; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; 3.1: |Suzuki-Miyaura Coupling / 3.2: |Suzuki-Miyaura Coupling / 6.1: |Johnson-Claisen Rearrangement;

DOI:10.1002/chem.201203284

Reference yield:

(5R,6S)-5-((tert-butyldimethylsilyl)oxy)-6-((4-methoxybenzyl)oxy)cyclohex-2-enone (1440947-46-5) → N-(2-(3-hydroxy-5-methoxy-3,3a,3a1,9a-tetrahydrophenanthro[4,5-bcd]furan-3a1-yl)ethyl)-N,4-dimethylbenzenesulfonamide (1440947-69-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: L-Selectride / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

1.2: 0.33 h / -78 - 20 °C / Inert atmosphere

2.1: triphenylphosphine; sodium carbonate; palladium diacetate / water; 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

2.2: 3.5 h / 20 °C / Inert atmosphere

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.75 h / 0 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

5.1: 2-hydroxynitrobenzene / 91 h / 140 - 170 °C / Inert atmosphere; Sealed tube

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h / 60 °C / Inert atmosphere

8.1: silver trifluoromethanesulfonate; Phenylselenyl chloride; boron trifluoride diethyl etherate / ethyl acetate / 1 h / 0 - 20 °C / Inert atmosphere

8.2: 1.5 h / 0 - 20 °C / Inert atmosphere

9.1: methanol; cerium(III) chloride heptahydrate / 0.5 h / 0 - 20 °C / Inert atmosphere

9.2: 0.33 h / 0 °C / Inert atmosphere

10.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

11.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

12.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

12.2: 0.25 h / -78 °C / Inert atmosphere

13.1: toluene-4-sulfonic acid / 1,2-dichloro-ethane / 15 h / 20 °C / Inert atmosphere

14.1: methanol; water / 0.17 h / 20 °C / Inert atmosphere

14.2: 0.25 h / 0 - 20 °C / Inert atmosphere

15.1: dmap; pyridine / 3 h / 80 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; methanol; dmap; lithium aluminium tetrahydride; Phenylselenyl chloride; oxalyl dichloride; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; palladium diacetate; L-Selectride; sodium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2-hydroxynitrobenzene; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; 2.1: |Suzuki-Miyaura Coupling / 2.2: |Suzuki-Miyaura Coupling / 5.1: |Johnson-Claisen Rearrangement;

DOI:10.1002/chem.201203284

upstream raw materials:

(5R,6S)-5-((tert-butyldimethylsilyl)oxy)-6-((4-methoxybenzyl)oxy)cyclohex-2-enone

(5R,6S)-5-((tert-butyldimethylsilyl)oxy)-6-((4-methoxybenzyl)oxy)cyclohex-1-en-1-yltrifluoromethanesulfonate

tert-butyl(((2R,3R)-2',3'-dimethoxy-2-((4-methoxybenzyl)oxy)-2,3,4,5-tetrahydro-[1,1'-biphenyl]-3-yl)oxy)dimethylsilane

(2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-ol

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