Benzoic acid, 2-methoxy-6-(2-propenyl)-, (1S,3R,4S)-1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-(methoxy methoxy)-4-methyl-6-heptenyl ester

Base Information

Chemical Name:Benzoic acid, 2-methoxy-6-(2-propenyl)-, (1S,3R,4S)-1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-(methoxy methoxy)-4-methyl-6-heptenyl ester
CAS No.:667865-89-6
Molecular Formula:C29H48O6Si
Molecular Weight:520.782
Hs Code.:

Benzoic acid, 2-methoxy-6-(2-propenyl)-,
(1S,3R,4S)-1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-(methoxy
methoxy)-4-methyl-6-heptenyl ester

Synonyms:

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Chemical Property of Benzoic acid, 2-methoxy-6-(2-propenyl)-, (1S,3R,4S)-1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-(methoxy methoxy)-4-methyl-6-heptenyl ester

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Technology Process of Benzoic acid, 2-methoxy-6-(2-propenyl)-, (1S,3R,4S)-1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-(methoxy methoxy)-4-methyl-6-heptenyl ester

There total 36 articles about Benzoic acid, 2-methoxy-6-(2-propenyl)-, (1S,3R,4S)-1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-(methoxy methoxy)-4-methyl-6-heptenyl 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: 90.0%

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

: 667865-70-5
1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-6-methyl-(3R,5R,6S)-8-nonen-3-ol

: 667865-89-6
1-[2-(tert-butyldimethylsilyloxy)ethyl]-3-methoxymethoxy-4-methyl-(1S,3R,4S)-6-heptenyl 2-allyl-6-methoxybenzoate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In benzene; at 20 ℃; for 2h;
DOI:10.2174/157017810791824856

Reference yield:

: 667865-73-8
5,7-di(benzyloxy)-(5S)-2-heptynyl alcohol

: 667865-89-6
1-[2-(tert-butyldimethylsilyloxy)ethyl]-3-methoxymethoxy-4-methyl-(1S,3R,4S)-6-heptenyl 2-allyl-6-methoxybenzoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 89.6 percent / LiAlH₄ / tetrahydrofuran / 8 h / Heating

2.1: 89.8 percent / D-(-)-diisopropyl tartrate; Ti(OⁱPr)4; TBHP / activated molecular sieves 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 12 h / -20 °C

3.1: 95 percent / I₂; triphenylphosphine; imidazole / acetonitrile; diethyl ether / 0.33 h / 0 °C

4.1: 91.6 percent / Zn; NaI / methanol / 8 h / Heating

5.1: 89.8 percent / NBS / CH₂Cl₂ / 5 h / 0 °C

6.1: 93 percent / n-tributyltinhydride; azobisisobutyronitrile / toluene / 2 h / Heating

7.1: 89.9 percent / aq. AcOH / 4 h / Heating

8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 85.8 percent / tetrahydrofuran; hexane / -78 - 0 °C

9.1: 92.2 percent / diisopropylethyl amine / CH₂Cl₂ / 3 h / 0 °C

10.1: 90.6 percent / lithium; liq. NH₃ / tetrahydrofuran / 1 h / -33 °C

11.1: 91.9 percent / imidazole / CH₂Cl₂ / 6 h / 0 - 20 °C

12.1: 74.3 percent / triphenylphosphine; DEAD / benzene / 14 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); ammonia; iodine; tri-n-butyl-tin hydride; lithium; D-(-)-diisopropyl tartrate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; zinc; diethylazodicarboxylate; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene; 2.1: Sharpless asymmetric epoxidation / 8.2: Wittig olefination / 12.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2003.10.038

Reference yield:

: 667865-71-6
(S)-1-(benzyloxy)-7-(tetrahydro-2H-pyran-2-yloxy)hept-5-yn-3-ol

: 667865-89-6
1-[2-(tert-butyldimethylsilyloxy)ethyl]-3-methoxymethoxy-4-methyl-(1S,3R,4S)-6-heptenyl 2-allyl-6-methoxybenzoate

Guidance literature:: Multi-step reaction with 14 steps

1.1: 97 percent / NaH; TBAI / tetrahydrofuran / 0 - 20 °C

2.1: 96.8 percent / para-toluenesulphonic acid / methanol / 2 h / 20 °C

3.1: 89.6 percent / LiAlH₄ / tetrahydrofuran / 8 h / Heating

4.1: 89.8 percent / D-(-)-diisopropyl tartrate; Ti(OⁱPr)4; TBHP / activated molecular sieves 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 12 h / -20 °C

5.1: 95 percent / I₂; triphenylphosphine; imidazole / acetonitrile; diethyl ether / 0.33 h / 0 °C

6.1: 91.6 percent / Zn; NaI / methanol / 8 h / Heating

7.1: 89.8 percent / NBS / CH₂Cl₂ / 5 h / 0 °C

8.1: 93 percent / n-tributyltinhydride; azobisisobutyronitrile / toluene / 2 h / Heating

9.1: 89.9 percent / aq. AcOH / 4 h / Heating

10.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

10.2: 85.8 percent / tetrahydrofuran; hexane / -78 - 0 °C

11.1: 92.2 percent / diisopropylethyl amine / CH₂Cl₂ / 3 h / 0 °C

12.1: 90.6 percent / lithium; liq. NH₃ / tetrahydrofuran / 1 h / -33 °C

13.1: 91.9 percent / imidazole / CH₂Cl₂ / 6 h / 0 - 20 °C

14.1: 74.3 percent / triphenylphosphine; DEAD / benzene / 14 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); ammonia; iodine; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; zinc; diethylazodicarboxylate; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene; 4.1: Sharpless asymmetric epoxidation / 10.2: Wittig olefination / 14.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2003.10.038