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

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]-propionaldehyde
CAS No.:853563-02-7
Molecular Formula:C₂₇H₄₁BrO₄
Molecular Weight:509.524
Hs Code.:

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]-propionaldehyde

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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]-propionaldehyde

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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]-propionaldehyde

There total 8 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]-propionaldehyde 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: 90.0%

: 853563-11-8
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

: 853563-02-7
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]-propionaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ol0504650

Reference yield:

: 853563-09-4
(R)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-pent-4-en-2-ol

: 853563-02-7
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]-propionaldehyde

Guidance literature:: Multi-step reaction with 8 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

8: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

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; Dess-Martin periodane; Rh/Al₂O₃; In tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 8: Dess-Martin oxidation;
DOI:10.1021/ol0504650

Reference yield:

: 853562-97-7
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

: 853563-02-7
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]-propionaldehyde

Guidance literature:: Multi-step reaction with 7 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

7: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

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; Dess-Martin periodane; Rh/Al₂O₃; In tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane; 7: Dess-Martin oxidation;
DOI:10.1021/ol0504650