(1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

Base Information

Chemical Name:(1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde
CAS No.:392235-18-6
Molecular Formula:C₂₃H₃₆O₃Si
Molecular Weight:388.623
Hs Code.:

Synonyms:(1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

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Chemical Property of (1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

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Technology Process of (1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

There total 7 articles about (1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-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%

: 392235-16-4
(1S,3aS,5S,7aR)-1-hydroxymethyl-5-(3-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a-ol

: 392235-18-6
(1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; for 1.5h;
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

: 392235-18-6
(1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

Guidance literature:: Multi-step reaction with 7 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: tert-butyllithium / diethyl ether; pentane / 1.33 h / -78 - 0 °C

5.2: 61 percent / diethyl ether; pentane; tetrahydrofuran / 0.5 h / -78 °C

6.1: 66 percent / Raney-Ni / ethanol / 8 h / Heating

7.1: 100 percent / IBX / dimethylsulfoxide / 1.5 h

With borane; potassium tert-butylate; tert.-butyl lithium; oxalic acid; nickel; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; ethanol; water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol; pentane; 2.1: Wittig reaction;
DOI:10.1021/jm011001k

Reference yield:

: 178379-39-0
(1S,3aS,7aR)-1-hydroxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone

: 392235-18-6
(1S,3aS,5S,7aR)-5-(3-tert-butyldimethylsilyloxyphenyl)-3a-hydroxy-7a-methylperhydroindene-1-carboxaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1.1: tert-butyllithium / diethyl ether; pentane / 1.33 h / -78 - 0 °C

1.2: 61 percent / diethyl ether; pentane; tetrahydrofuran / 0.5 h / -78 °C

2.1: 66 percent / Raney-Ni / ethanol / 8 h / Heating

3.1: 100 percent / IBX / dimethylsulfoxide / 1.5 h

With tert.-butyl lithium; nickel; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In diethyl ether; ethanol; dimethyl sulfoxide; pentane;
DOI:10.1021/jm011001k