2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester

Base Information

Chemical Name:2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester
CAS No.:420794-45-2
Molecular Formula:C₃₃H₅₈O₅Si₂
Molecular Weight:590.992
Hs Code.:

2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester

Synonyms:2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester

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Chemical Property of 2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester

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Technology Process of 2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester

There total 16 articles about 2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl 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:

Reference yield: 63.0%

: 325172-28-9
2-allyl-6-methoxy-benzoic acid

: 398477-96-8
(3R,5S,6R)-1,5-bis-(tert-butyldimethylsilyloxy)-6-methylnon-8-en-3-ol

: 420794-45-2
2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; for 2h; Heating;
DOI:10.1021/ja0177713

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 420794-45-2
2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -10 - 20 °C

2: 84 percent / LiEt₃BH / tetrahydrofuran / 7 h / -78 - -40 °C

3: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

4: 86 percent / LiEt₃BH / tetrahydrofuran / 16 h / 20 °C

5: 85 percent / Bu₃SnH; AIBN / toluene / 2 h / 90 °C

6: 96 percent / DDQ / CH₂Cl₂; H₂O / 0.17 h / 20 °C

7: 63 percent / DEAD; PPh₃ / diethyl ether / 2 h / Heating

With 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium triethylborohydride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; 7: Mitsunobu esterification;
DOI:10.1021/ja0177713

Reference yield:

: 89922-82-7
3-(tert-butyldimethylsilanyloxy)propionaldehyde

: 420794-45-2
2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methylhept-6-enyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: Et₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -5 °C

1.2: 66 percent / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 72 percent / TfOH / diethyl ether / 2 h / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

4.2: 74 percent / CH₂Cl₂ / 2 h / -78 °C

5.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -10 - 20 °C

6.1: 84 percent / LiEt₃BH / tetrahydrofuran / 7 h / -78 - -40 °C

7.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

8.1: 86 percent / LiEt₃BH / tetrahydrofuran / 16 h / 20 °C

9.1: 85 percent / Bu₃SnH; AIBN / toluene / 2 h / 90 °C

10.1: 96 percent / DDQ / CH₂Cl₂; H₂O / 0.17 h / 20 °C

11.1: 63 percent / DEAD; PPh₃ / diethyl ether / 2 h / Heating

With 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; tri-n-butyl-tin hydride; titanium tetrachloride; diisobutylaluminium hydride; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylboron trifluoromethanesulfonate; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; 11.1: Mitsunobu esterification;
DOI:10.1021/ja0177713