(2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane

Base Information

• Chemical Name: (2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane
• CAS No.: 853563-00-5
• Molecular Formula: C₂₇H₄₁BrO₃
• Molecular Weight: 493.525
• Mol file: 853563-00-5.mol

Synonyms:(2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane

Chemical Property of (2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane

There total 5 articles about (2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane 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:

(R)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-pent-4-en-2-ol (853563-09-4) → (2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane (853563-00-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / imidazole / dimethylformamide / 3.5 h

2: 59 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / 1,2-dichloro-ethane / 2 h / 40 °C

3: 73 percent / H₂ / Rh/Al₂O₃ / ethanol / 5 h / 760 Torr

4: TBAF / tetrahydrofuran / 7 h

5: 133 mg / t-BuOK / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; Rh/Al₂O₃; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0504650

Reference yield:

tert-Butyl-[(R)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane (853562-97-7) → (2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane (853563-00-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 59 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / 1,2-dichloro-ethane / 2 h / 40 °C

2: 73 percent / H₂ / Rh/Al₂O₃ / ethanol / 5 h / 760 Torr

3: TBAF / tetrahydrofuran / 7 h

4: 133 mg / t-BuOK / tetrahydrofuran / 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; Rh/Al₂O₃; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane;

DOI:10.1021/ol0504650

Reference yield:

[(E)-(R)-4-(4-Bromo-phenyl)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane (853563-10-7) → (2S,6S,7S,10R)-2-[(R)-2-Allyloxy-5-(4-bromo-phenyl)-pentyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecane (853563-00-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / H₂ / Rh/Al₂O₃ / ethanol / 5 h / 760 Torr

2: TBAF / tetrahydrofuran / 7 h

3: 133 mg / t-BuOK / tetrahydrofuran / 2 h / 20 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; Rh/Al₂O₃; In tetrahydrofuran; ethanol;

DOI:10.1021/ol0504650

upstream raw materials:

allyl bromide

(R)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-pent-4-en-2-ol

tert-Butyl-[(R)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane

[(E)-(R)-4-(4-Bromo-phenyl)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane

Downstream raw materials:

3-[(R)-4-(4-Bromo-phenyl)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-butoxy]-propionaldehyde

3-[(R)-4-(4-Bromo-phenyl)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-butoxy]-propan-1-ol

((S)-1-{2-[(R)-4-(4-Bromo-phenyl)-1-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-butoxy]-ethyl}-but-3-enyloxy)-tert-butyl-dimethyl-silane