(3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol

Base Information

• Chemical Name: (3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol
• CAS No.: 263138-41-6
• Molecular Formula: C₃₂H₅₆O₉
• Molecular Weight: 584.791

Synonyms:(3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol

Chemical Property of (3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol

There total 21 articles about (3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol 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: 93.0%

(2S,3R)-2-Iodomethyl-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxirane (263138-40-5) → (3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol (263138-41-6)

Guidance literature:

With iodine; zinc; In methanol; Heating;

DOI:10.1021/jo991689x

Reference yield:

(2S,3R,4R)-(+)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-hexyn-3-ol (263138-21-2) → (3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol (263138-41-6)

Guidance literature:

Multi-step reaction with 18 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

15.1: 93 percent / DIBAL-H / CH₂Cl₂; various solvent(s) / 0.67 h

16.1: 91 percent / t-BuOOH; Ti(O-i-Pr)4; (-)-i-Pr tartrate / CH₂Cl₂; decane / 16 h / -20 °C

17.1: 96 percent / I₂; imidazole; PPh₃ / benzene; diethyl ether / 0.25 h

18.1: 93 percent / Zn; I₂ / methanol / Heating

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; 15-crown-5; N,N-diethyl-N-isopropylamine; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; iodine; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; decane; 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 / 15.1: Reduction / 16.1: Oxidation / 17.1: Substitution / 18.1: Elimination;

DOI:10.1021/jo991689x

Reference yield:

(2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-3-methoxymethoxy-5-hexyne (263138-22-3) → (3S,4R,5S,6S,9R,10S,11R,12R)-14-(4-Methoxy-benzyloxy)-5,9,11-tris-methoxymethoxy-4,6,10,12-tetramethyl-tetradec-1-en-3-ol (263138-41-6)

Guidance literature:

Multi-step reaction with 17 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

14.1: 93 percent / DIBAL-H / CH₂Cl₂; various solvent(s) / 0.67 h

15.1: 91 percent / t-BuOOH; Ti(O-i-Pr)4; (-)-i-Pr tartrate / CH₂Cl₂; decane / 16 h / -20 °C

16.1: 96 percent / I₂; imidazole; PPh₃ / benzene; diethyl ether / 0.25 h

17.1: 93 percent / Zn; I₂ / methanol / Heating

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; 15-crown-5; N,N-diethyl-N-isopropylamine; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; iodine; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; Dess-Martin periodane; toluene-4-sulfonic acid hydrazide; triphenylphosphine; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; decane; 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 / 14.1: Reduction / 15.1: Oxidation / 16.1: Substitution / 17.1: Elimination;

DOI:10.1021/jo991689x

upstream raw materials:

(2S,3R)-2-Iodomethyl-3-[(1S,2S,3S,6R,7S,8R,9R)-11-(4-methoxy-benzyloxy)-2,6,8-tris-methoxymethoxy-1,3,7,9-tetramethyl-undecyl]-oxirane

p-methoxybenzyl chloride

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

(2R,3S,4S)-1-(tert-butyldiphenylsilyloxy)-2,4-dimethyl-5-hexyn-3-ol

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