(2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester
• CAS No.: 179944-14-0
• Molecular Formula: C₃₅H₅₆O₆Si
• Molecular Weight: 600.912
• Mol file: 179944-14-0.mol

Synonyms:(2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

Chemical Property of (2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

There total 12 articles about (2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl 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:

[2-((S)-1-Benzyloxymethyl-propoxymethoxy)-ethyl]-trimethyl-silane (179944-03-7) → (2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester (179944-14-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / H₂ / Pd(OH)2 on C / tetrahydrofuran; methanol

2: 75 percent / PDC / dimethylformamide / Ambient temperature

3: 92 percent / diethyl ether / 0 °C

4: CrCl₂ / tetrahydrofuran / 0 °C

5: 1.) t-BuLi / 1.) ether, pentane, -78 deg C, 90 min, 2.) ether, THF, pentane, -78 deg C, 2 h

6: 1.) Martin's sulfurane reagent, 2.) Et₄NF / 1.) CH₂Cl₂, RT, 2.) DMF, RT, overnight

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

8: 1.) LiCl, DBU / 1.) CH₃CN, RT, 2.) CH₃CN, 0 deg C, 1 h

9: 96 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

10: I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / -30 °C

11: LiHMDS, HMPA / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; oxalyl dichloride; Martins sulfurane; hydrogen; iodine; tert.-butyl lithium; diisobutylaluminium hydride; tetraethylammonium fluoride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja961344l

Reference yield:

(2R,4S)-2-(2,4,6-Trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester (179944-11-7) + [2-((2E,7E)-(1S,6S)-1-Ethyl-9-iodo-2,6,8-trimethyl-4-methylene-nona-2,7-dienyloxymethoxy)-ethyl]-trimethyl-silane (179944-13-9) → (2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester (179944-14-0)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Yield given;

DOI:10.1021/ja961344l

Reference yield:

(S)-2-(2-Trimethylsilanyl-ethoxymethoxy)-butan-1-ol (594855-23-9) → (2R,4S)-4-[(2E,7E)-(4S,9S)-2,4,8-Trimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienyl]-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester (179944-14-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 75 percent / PDC / dimethylformamide / Ambient temperature

2: 92 percent / diethyl ether / 0 °C

3: CrCl₂ / tetrahydrofuran / 0 °C

4: 1.) t-BuLi / 1.) ether, pentane, -78 deg C, 90 min, 2.) ether, THF, pentane, -78 deg C, 2 h

5: 1.) Martin's sulfurane reagent, 2.) Et₄NF / 1.) CH₂Cl₂, RT, 2.) DMF, RT, overnight

6: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

7: 1.) LiCl, DBU / 1.) CH₃CN, RT, 2.) CH₃CN, 0 deg C, 1 h

8: 96 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

9: I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / -30 °C

10: LiHMDS, HMPA / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; oxalyl dichloride; Martins sulfurane; iodine; tert.-butyl lithium; diisobutylaluminium hydride; tetraethylammonium fluoride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja961344l

upstream raw materials:

(2R,4S)-2-(2,4,6-Trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

[2-((2E,7E)-(1S,6S)-1-Ethyl-9-iodo-2,6,8-trimethyl-4-methylene-nona-2,7-dienyloxymethoxy)-ethyl]-trimethyl-silane

(S)-2-(2-Trimethylsilanyl-ethoxymethoxy)-butan-1-ol

5-(tert-butyldimethylsilanyloxy)-4(S)-methylpentan-2-one

Downstream raw materials:

(11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

(11E,16E)-(2R,5S,7S,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

galbonolide B

(2R,4S)-4-((2E,7E)-(4S,9S)-9-Acetoxy-2,4,8-trimethyl-6-methylene-undeca-2,7-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester