(1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.0^1.6]deca-4-en-6-ol

Base Information

• Chemical Name: (1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.0^1.6]deca-4-en-6-ol
• CAS No.: 350231-11-7
• Molecular Formula: C₃₀H₄₀O₂Si
• Molecular Weight: 460.732

Synonyms:(1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.0^1.6]deca-4-en-6-ol

Chemical Property of (1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.0^1.6]deca-4-en-6-ol

Chemical Property:

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Technology Process of (1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.0^1.6]deca-4-en-6-ol

There total 4 articles about (1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.0^1.6]deca-4-en-6-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: 60.0%

(1S)-{1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-vinyl}-6-isopropenyl-3-methyl-cyclohex-2-enol (350231-10-6) → (1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.01.6]deca-4-en-6-ol (350231-11-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 220 ℃; for 5h;

DOI:10.1021/ol015970l

Reference yield:

(1S)-{1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-vinyl}-6-isopropenyl-3-methyl-cyclohex-2-enol (350231-10-6) → 4-[2-(t-butyl-diphenyl-silanyloxy)-ethyl]-6-methyl-1-methylene-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-ol + (1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.01.6]deca-4-en-6-ol (350231-11-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 220 ℃; for 1h; Title compound not separated from byproducts; microwave irradiation;

DOI:10.1021/jo047916z

Reference yield:

tert-butyl((3-iodobut-3-en-1-yl)oxy)diphenylsilane (848122-40-7) → (1R,6R,7R)-7-[2-(tert-butyl-diphenylsilanyloxy)-ethyl]-10-methylene-4-methylbicyclo[4.4.01.6]deca-4-en-6-ol (350231-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuLi / diethyl ether / 0.17 h / -90 °C

1.2: 89 percent / diethyl ether / -90 - -40 °C

2.1: DBU / toluene / 1 h / 220 °C / microwave irradiation

With tert.-butyl lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; toluene;

DOI:10.1021/jo047916z

upstream raw materials:

(1S)-{1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-vinyl}-6-isopropenyl-3-methyl-cyclohex-2-enol

(S)-isopiperitenone

tert-butyl((3-iodobut-3-en-1-yl)oxy)diphenylsilane

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