(1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

Base Information

Chemical Name:(1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde
CAS No.:392235-33-5
Molecular Formula:C₂₃H₄₂O₃Si
Molecular Weight:394.67
Hs Code.:

Synonyms:(1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

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Chemical Property of (1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

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Technology Process of (1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

There total 13 articles about (1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde 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: 100.0%

: 392235-32-4
(1S,3aS,5S,7aR)-1-hydroxymethyl-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-7a-methylperhydroindene-3a-ol

: 392235-33-5
(1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; for 1h; Heating;
DOI:10.1021/jm011001k

Reference yield:

: 67963-68-2
t-butyldimethylsilyl-4-bromophenol

: 392235-33-5
(1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-butyllithium / hexane / 4 h / 20 °C

1.2: 43 percent / hexane; tetrahydrofuran / 1.5 h / -78 °C

2.1: 53 percent / Ranye-Ni / ethanol / 8 h / Heating

3.1: 50 percent / H₂ / 5percent Rh/Al₂O₃ / methanol / 24 h / 3268.22 Torr

4.1: 100 percent / pyridine; DMAP / 16 h / 20 °C

5.1: 58 percent / aq. HCl / dioxane / 1.5 h / 20 °C / pH 1

6.1: 100 percent / IBX / tetrahydrofuran / 1 h / Heating

7.1: LiAlH(OtBut)3 / tetrahydrofuran / 4 h / -78 - 20 °C

8.1: imidazole / dimethylformamide / 3 h

9.1: 100 percent / 10percent aq. K₂CO₃ / methanol / 2 h / 20 °C

10.1: 100 percent / IBX / tetrahydrofuran / 1 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; dmap; n-butyllithium; Ranye-Ni; hydrogen; lithium tri-t-butoxyaluminum hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 5percent Rh/Al₂O₃; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; N,N-dimethyl-formamide;
DOI:10.1021/jm011001k

Reference yield:

: 33879-04-8,51065-67-9
(+)-(3aS,7aS)-2,3,3a,4,7,7a-hexahydro-3a-hydroxy-7a-methyl-1H-indene-1,5(6H)-dione

: 392235-33-5
(1S,3aS,5S,7aR)-5-(4-trans-tert-butyldimethylsilyoxy-1-cyclohexyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

Guidance literature:: Multi-step reaction with 14 steps

1.1: 83 percent / oxalic acid / acetonitrile / 16 h

2.1: 77 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Heating

3.1: BH₃ / tetrahydrofuran / 1 h / 20 °C

3.2: 20 percent / NaBO₃; aq. NaOH / 16 h / 20 °C

4.1: 68 percent / 1 N pTSA / acetonitrile; H₂O / 16 h

5.1: n-butyllithium / hexane / 4 h / 20 °C

5.2: 43 percent / hexane; tetrahydrofuran / 1.5 h / -78 °C

6.1: 53 percent / Ranye-Ni / ethanol / 8 h / Heating

7.1: 50 percent / H₂ / 5percent Rh/Al₂O₃ / methanol / 24 h / 3268.22 Torr

8.1: 100 percent / pyridine; DMAP / 16 h / 20 °C

9.1: 58 percent / aq. HCl / dioxane / 1.5 h / 20 °C / pH 1

10.1: 100 percent / IBX / tetrahydrofuran / 1 h / Heating

11.1: LiAlH(OtBut)3 / tetrahydrofuran / 4 h / -78 - 20 °C

12.1: imidazole / dimethylformamide / 3 h

13.1: 100 percent / 10percent aq. K₂CO₃ / methanol / 2 h / 20 °C

14.1: 100 percent / IBX / tetrahydrofuran / 1 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; dmap; n-butyllithium; Ranye-Ni; borane; potassium tert-butylate; hydrogen; oxalic acid; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 5percent Rh/Al₂O₃; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 2.1: Wittig reaction;
DOI:10.1021/jm011001k