(E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl ester
CAS No.:263138-37-0
Molecular Formula:C₃₄H₅₈O₁₀
Molecular Weight:626.829
Hs Code.:

Synonyms:(E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl ester

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Chemical Property of (E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl ester

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Technology Process of (E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl ester

There total 17 articles about (E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl 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: 99.0%

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 263138-36-9
(2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal

: 263138-37-0
(E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl ester

Guidance literature:: In dichloromethane; for 20h; Heating;
DOI:10.1021/jo991689x

Reference yield:

: 263138-21-2
(2S,3R,4R)-(+)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-hexyn-3-ol

: 263138-37-0
(E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 96 percent / i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 48 h / 20 °C

2.1: (c-C₆H₁₁)2BH / 1,2-dimethoxy-ethane / 6.5 h / 20 °C

2.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

3.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

4.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

5.1: 71 percent / Bu₄NF / tetrahydrofuran / 24 h / 20 °C

6.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h

7.1: BuLi / tetrahydrofuran; hexane / -78 - -40 °C

7.2: 43 percent / LiBr / tetrahydrofuran; hexane / 1 h / -35 °C

8.1: 59 percent / i-PrO₂CN=NCO₂-i-Pr; Ph₃P / benzene / 18 h / 20 °C

9.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h

10.1: 95 percent / TsNHNH₂; NaOAc / 1,2-dimethoxy-ethane; H₂O / Heating

11.1: 99 percent / i-PrNEt₂; Bu₄NI / CH₂Cl₂ / 42 h / 20 °C

12.1: 96 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

13.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

14.1: 99 percent / CH₂Cl₂ / 20 h / Heating

With n-butyllithium; 15-crown-5; N,N-diethyl-N-isopropylamine; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; benzene; 1.1: Etherification / 2.1: Addition / 2.2: Oxidation / 3.1: Reduction / 4.1: Etherification / 5.1: Hydrolysis / 6.1: Oxidation / 7.1: Metallation / 7.2: Addition / 8.1: Esterification / 9.1: Hydrolysis / 10.1: Hydrogenation / 11.1: Etherification / 12.1: Hydrolysis / 13.1: Oxidation / 14.1: Condensation;
DOI:10.1021/jo991689x

Reference yield:

: 263138-22-3
(2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-3-methoxymethoxy-5-hexyne

: 263138-37-0
(E)-(4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: (c-C₆H₁₁)2BH / 1,2-dimethoxy-ethane / 6.5 h / 20 °C

1.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

2.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

3.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

4.1: 71 percent / Bu₄NF / tetrahydrofuran / 24 h / 20 °C

5.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h

6.1: BuLi / tetrahydrofuran; hexane / -78 - -40 °C

6.2: 43 percent / LiBr / tetrahydrofuran; hexane / 1 h / -35 °C

7.1: 59 percent / i-PrO₂CN=NCO₂-i-Pr; Ph₃P / benzene / 18 h / 20 °C

8.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h

9.1: 95 percent / TsNHNH₂; NaOAc / 1,2-dimethoxy-ethane; H₂O / Heating

10.1: 99 percent / i-PrNEt₂; Bu₄NI / CH₂Cl₂ / 42 h / 20 °C

11.1: 96 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

12.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

13.1: 99 percent / CH₂Cl₂ / 20 h / Heating

With n-butyllithium; 15-crown-5; N,N-diethyl-N-isopropylamine; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; benzene; 1.1: Addition / 1.2: Oxidation / 2.1: Reduction / 3.1: Etherification / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Esterification / 8.1: Hydrolysis / 9.1: Hydrogenation / 10.1: Etherification / 11.1: Hydrolysis / 12.1: Oxidation / 13.1: Condensation;
DOI:10.1021/jo991689x