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

Base Information

• Chemical Name: 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
• CAS No.: 853563-11-8
• Molecular Formula: C₂₇H₄₃BrO₄
• Molecular Weight: 511.54

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 7 articles about 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 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) → 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 (853563-11-8)

Guidance literature:

Multi-step reaction with 7 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

6: tetrahydrofuran / 4.5 h / 20 °C

7: 102 mg / aq. H₂O₂; NaOH / tetrahydrofuran / 2 h

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydroxide; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; 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) → 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 (853563-11-8)

Guidance literature:

Multi-step reaction with 6 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

5: tetrahydrofuran / 4.5 h / 20 °C

6: 102 mg / aq. H₂O₂; NaOH / tetrahydrofuran / 2 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydroxide; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; 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) → 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 (853563-11-8)

Guidance literature:

Multi-step reaction with 5 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

4: tetrahydrofuran / 4.5 h / 20 °C

5: 102 mg / aq. H₂O₂; NaOH / tetrahydrofuran / 2 h

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

DOI:10.1021/ol0504650

upstream raw materials:

(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

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

[(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:

((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

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

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