diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate

Base Information

Chemical Name:diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate
CAS No.:1004999-93-2
Molecular Formula:C₂₂H₃₀O₆
Molecular Weight:390.477
Hs Code.:

Synonyms:diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate

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Chemical Property of diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate

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Technology Process of diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate

There total 7 articles about diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate 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: 57.0%

: 1005000-03-2
ethyl 2-((2S,5R)-5-hydroxy-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate

: 78-39-7
Triethyl orthoacetate

: 1004999-93-2
diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate

Guidance literature:: With 2-hydroxynitrobenzene; at 140 ℃; for 120h;
DOI:10.1016/j.tetlet.2007.11.037

Reference yield: 36.0%

: 1004999-94-3
(2R,3R)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2,3-diol

: 78-39-7
Triethyl orthoacetate

: 1004999-93-2
diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate

Guidance literature:: With 2-hydroxynitrobenzene; at 140 ℃; for 72h;
DOI:10.1016/j.tetlet.2007.11.037

Reference yield:

: (2S,3R)-3-((tert-butyldimethylsilyl)oxy)-5-hydroxy-2-((4-methoxybenzyl)oxy)cyclohexanone

: 1004999-93-2
diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate

Guidance literature:: Multi-step reaction with 6 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

With dmap; tetrabutyl ammonium fluoride; palladium diacetate; L-Selectride; sodium carbonate; methanesulfonyl chloride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2-hydroxynitrobenzene; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 3.1: |Suzuki-Miyaura Coupling / 3.2: |Suzuki-Miyaura Coupling / 6.1: |Johnson-Claisen Rearrangement;
DOI:10.1002/chem.201203284