2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole

Base Information

• Chemical Name: 2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole
• CAS No.: 322428-87-5
• Molecular Formula: C₃₇H₅₀N₂O₇
• Molecular Weight: 634.813
• Mol file: 322428-87-5.mol

Synonyms:2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole

Chemical Property of 2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole

There total 52 articles about 2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole 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:

2-((3E,6Z,9E)-(S)-6,8-Dimethyl-undeca-3,6,9-trienyl)-oxazole-4-carboxylic acid {(R)-1-formyl-2-methoxy-3-[(2R,4R,6R)-6-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-propyl}-amide → 2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole (322428-87-5)

Guidance literature:

2-((3E,6Z,9E)-(S)-6,8-Dimethyl-undeca-3,6,9-trienyl)-oxazole-4-carboxylic acid {(R)-1-formyl-2-methoxy-3-[(2R,4R,6R)-6-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-propyl}-amide; With 2,6-di-tert-butyl-pyridine; 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.5h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; at 0 - 20 ℃; for 1h;

DOI:10.1016/S0040-4020(01)00593-2

Reference yield:

(4E)-5-iodo-pent-4-en-1-ol (93782-93-5) → 2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole (322428-87-5)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 80 percent / i-Pr₂NEt / CH₂Cl₂ / 15.5 h / 0 - 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C

2.2: 53 percent / HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.1: 90 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

4.1: Py*SO₃; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0 - 20 °C

5.1: 142 mg / CrCl₂ / tetrahydrofuran / 0.83 h / 20 °C

6.1: 100 percent / Pd(Ph₃P)4 / tetrahydrofuran / 1.5 h / 20 °C

7.1: 83 percent / HCl / tetrahydrofuran; H₂O / 6 h / 20 °C

8.1: 72 percent / pyridinium dichromate / dimethylformamide / 3.5 h / 20 °C

9.1: 91 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 3.5 h / 0 - 20 °C

10.1: bis(2-methoxyethyl)aminosulfur trifluoride / CH₂Cl₂ / 0.42 h / -20 °C

11.1: 21 mg / BrCCl₃; DBU / CH₂Cl₂ / 14 h / 0 - 20 °C

12.1: 100 percent / LiOH; H₂O / tetrahydrofuran / 1.33 h / 0 - 20 °C

13.1: 39 mg / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 9.5 h / 0 - 20 °C

14.1: 27 mg / TBAF / tetrahydrofuran / 1.17 h / 0 - 20 °C

15.1: Dess-Martin periodinane / CH₂Cl₂ / 15 h / 20 °C

16.1: PPh₃; 2,6-di-tert-butylpyridine; BrCCl₂CCl₂Br / CH₂Cl₂ / 0.5 h / 0 °C

16.2: 16 mg / DBU / CH₂Cl₂; acetonitrile / 1 h / 0 - 20 °C

With chromium dichloride; hydrogenchloride; lithium hydroxide; dipyridinium dichromate; 2,6-di-tert-butyl-pyridine; 1,2-dibromo-1,1,2,2-tetrachloroethane; Bromotrichloromethane; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; sulfur trioxide pyridine complex; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane; 4.1: Parikh-Doering oxidation / 15.1: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(01)00593-2

Reference yield:

(1E)-5-(methoxymethyloxy)-1-pentenyl iodide (322428-68-2) → 2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole (322428-87-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C

1.2: 53 percent / HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.1: 90 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: Py*SO₃; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0 - 20 °C

4.1: 142 mg / CrCl₂ / tetrahydrofuran / 0.83 h / 20 °C

5.1: 100 percent / Pd(Ph₃P)4 / tetrahydrofuran / 1.5 h / 20 °C

6.1: 83 percent / HCl / tetrahydrofuran; H₂O / 6 h / 20 °C

7.1: 72 percent / pyridinium dichromate / dimethylformamide / 3.5 h / 20 °C

8.1: 91 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 3.5 h / 0 - 20 °C

9.1: bis(2-methoxyethyl)aminosulfur trifluoride / CH₂Cl₂ / 0.42 h / -20 °C

10.1: 21 mg / BrCCl₃; DBU / CH₂Cl₂ / 14 h / 0 - 20 °C

11.1: 100 percent / LiOH; H₂O / tetrahydrofuran / 1.33 h / 0 - 20 °C

12.1: 39 mg / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 9.5 h / 0 - 20 °C

13.1: 27 mg / TBAF / tetrahydrofuran / 1.17 h / 0 - 20 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 15 h / 20 °C

15.1: PPh₃; 2,6-di-tert-butylpyridine; BrCCl₂CCl₂Br / CH₂Cl₂ / 0.5 h / 0 °C

15.2: 16 mg / DBU / CH₂Cl₂; acetonitrile / 1 h / 0 - 20 °C

With chromium dichloride; hydrogenchloride; lithium hydroxide; dipyridinium dichromate; 2,6-di-tert-butyl-pyridine; 1,2-dibromo-1,1,2,2-tetrachloroethane; Bromotrichloromethane; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; sulfur trioxide pyridine complex; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane; 3.1: Parikh-Doering oxidation / 14.1: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(01)00593-2

upstream raw materials:

(4E)-5-iodo-pent-4-en-1-ol

(1E)-5-(methoxymethyloxy)-1-pentenyl iodide

(4E,7Z,9S,10E)-7,9-dimethyl-4,7,10-dodecatrienol

(2R,3Z,6E)-10-(methoxymethyloxy)-2,4-dimethyl-3,6-decadien-1-ol