(+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene

Base Information

• Chemical Name: (+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene
• CAS No.: 214218-32-3
• Molecular Formula: C₃₂H₅₀O₃Si₂
• Molecular Weight: 538.918

Synonyms:(+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene

Chemical Property of (+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene

There total 8 articles about (+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene 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: 96.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (+)-(2R)-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-en-1-ol (214218-31-2) → (+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene (214218-32-3)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1016/S0040-4020(98)00676-0

Reference yield:

(2-bromoallyl)trimethylsilane (81790-10-5) → (+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene (214218-32-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium / tetrahydrofuran / 0.5 h / Heating

1.2: 39 percent / tetrahydrofuran / 0 °C

2.1: 98 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂

3.1: 88 percent / di-iso-propylamine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butyldimethylsilyl chloride / tetrahydrofuran

4.1: 99 percent / sodium bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran; toluene / 1.5 h / 0 °C

5.1: 96 percent / 4-(dimethylamino)pyridine; imidazole / dimethylformamide / 20 h / 20 °C

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; magnesium; tert-butyldimethylsilyl chloride; triethylamine; diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Esterification / 3.1: Ireland Claisen rearrangement / 4.1: Reduction / 5.1: Etherification;

DOI:10.1016/S0040-4020(98)00676-0

Reference yield:

(S)-(-)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde (79243-92-8) → (+)-(2R)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-ene (214218-32-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium / tetrahydrofuran / 0.5 h / Heating

1.2: 39 percent / tetrahydrofuran / 0 °C

2.1: 98 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂

3.1: 88 percent / di-iso-propylamine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert-butyldimethylsilyl chloride / tetrahydrofuran

4.1: 99 percent / sodium bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran; toluene / 1.5 h / 0 °C

5.1: 96 percent / 4-(dimethylamino)pyridine; imidazole / dimethylformamide / 20 h / 20 °C

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; magnesium; tert-butyldimethylsilyl chloride; triethylamine; diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Esterification / 3.1: Ireland Claisen rearrangement / 4.1: Reduction / 5.1: Etherification;

DOI:10.1016/S0040-4020(98)00676-0

upstream raw materials:

tert-butylchlorodiphenylsilane

(+)-(2R)-2-methyl-5-[(4R')-2',2',4'-trimethyl-1',3'-dioxolan-4'-yl]-4-(trimethylsilylmethyl)pent-4-en-1-ol

(2-bromoallyl)trimethylsilane

(S)-(-)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde

Downstream raw materials:

(+)-Prelog-Djerassi lactonic acid

(+)-(2S,3S,4S,6R)-7-[(tert-butyldiphenylsilyl)oxy]-1,3-diacetoxy-2,4,6-trimethylheptane

(+)-(2S,3R,6R)-7-[(tert-butyldiphenylsilyl)oxy]-2,6-dimethyl-2,3-epoxy-4-methyleneheptan-1-ol

(-)-(2S,3S,4S,6R)-7-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethylheptan-1,3-diol

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