(1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane

Base Information

• Chemical Name: (1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane
• CAS No.: 1000669-80-6
• Molecular Formula: C₃₅H₅₂O₂Si₂
• Molecular Weight: 560.968

Synonyms:(1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane

Chemical Property of (1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane

There total 9 articles about (1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane 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:

(1R,2R)-1-{(R)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-7-trimethylsilanyl-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane → (1R,2R)-1-{(R)-(Z)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane + (1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane (1000669-80-6)

Guidance literature:

With potassium carbonate; In methanol; dichloromethane; at 23 ℃; for 21h;

DOI:10.1021/ja076165q

Reference yield:

C12H26O3Si → (1R,2R)-1-{(R)-(Z)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane + (1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane (1000669-80-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; diethyl ether; hexane / 1.5 h / -78 °C / Inert atmosphere

1.2: 6.5 h / -78 - 0 °C / Inert atmosphere

1.3: -78 - -50 °C / Inert atmosphere

2.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 1 h / 23 °C / Inert atmosphere

3.1: phenyllithium; lithium bromide / tetrahydrofuran; diethyl ether / 0.5 h / -78 - 23 °C / Inert atmosphere

3.2: 1 h / 0 - 23 °C / Inert atmosphere

4.1: methanol; potassium carbonate / dichloromethane / 21 h / 23 °C / Inert atmosphere

With 1H-imidazole; methanol; iodine; potassium carbonate; phenyllithium; triphenylphosphine; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1021/ja806724x

Reference yield:

C12H24O3Si (1088705-31-0) → (1R,2R)-1-{(R)-(Z)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane + (1R,2R)-1-{(R)-(E)-5-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-hept-1-en-6-ynyl}-2-[tert-butyl-diphenylsilanyloxymethyl]-cyclopropane (1000669-80-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran; diethyl ether; hexane / 1.5 h / -78 °C / Inert atmosphere

2.2: 6.5 h / -78 - 0 °C / Inert atmosphere

2.3: -78 - -50 °C / Inert atmosphere

3.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 1 h / 23 °C / Inert atmosphere

4.1: phenyllithium; lithium bromide / tetrahydrofuran; diethyl ether / 0.5 h / -78 - 23 °C / Inert atmosphere

4.2: 1 h / 0 - 23 °C / Inert atmosphere

5.1: methanol; potassium carbonate / dichloromethane / 21 h / 23 °C / Inert atmosphere

With 1H-imidazole; methanol; iodine; diisobutylaluminium hydride; potassium carbonate; phenyllithium; triphenylphosphine; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1021/ja806724x

upstream raw materials:

C₁₂H₂₄O₃Si

(4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-5-trimethylsilanyl-pent-4-yn-1-ol

(3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(2-iodo-ethyl)-1-trimethylsilanyl-pent-1-yne

(1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane

Downstream raw materials:

(1R,3aS,6R)-1-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-1,2,3,3a,6,7-hexahydro-azulene

C₃₅H₅₂O₂Si₂

(1R,6S)-1-[(R)-1-(tert-butyl-dimethylsilanyloxy)-ethyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-1,2,3,5,6,7-hexahydro-azulene

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