ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate

Base Information

Chemical Name:ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate
CAS No.:1005000-02-1
Molecular Formula:C₂₄H₃₈O₅Si
Molecular Weight:434.648
Hs Code.:

Synonyms:ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate

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Chemical Property of ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate

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Technology Process of ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate

There total 1 articles about ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate 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: 87.0%

: 1005000-01-0
(2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-ol

: 78-39-7
Triethyl orthoacetate

: 1005000-02-1
ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate

Guidance literature:: With propionic acid; at 140 ℃; for 24h;
DOI:10.1016/j.tetlet.2007.11.037

Reference yield: 97.0%

: 1005000-02-1
ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/j.tetlet.2007.11.037

Reference yield:

: 1005000-02-1
ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate

: 872033-94-8
N-(2-((3R,3aR,3a1S,9aS)-3-hydroxy-5-methoxy-1,2,3,3a,3a1,9a-hexahydrophenanthro[4,5-bcd]furan-3a1-yl)ethyl)-N,4-dimethylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 20 °C / Inert atmosphere

2.1: 2-hydroxynitrobenzene / 168 h / 140 °C / Inert atmosphere; Sealed tube

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C / Inert atmosphere

6.1: Montmorillonite K-10 / 1,2-dichloro-ethane / 24 h / 20 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine / dichloromethane / 0.83 h / 20 °C / Inert atmosphere

8.1: methylamine hydrochloride / methanol; tetrahydrofuran / 6 h / 0 °C / Inert atmosphere; Molecular sieve

8.2: 0.17 h / 0 °C / Inert atmosphere; Molecular sieve

9.1: dmap; pyridine / 4 h / 80 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 26 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; tetrabutyl ammonium fluoride; methylamine hydrochloride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; 2-hydroxynitrobenzene; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 2.1: |Johnson-Claisen Rearrangement / 6.1: |Friedel-Crafts Alkylation;
DOI:10.1002/chem.201203284