(1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

Base Information

Chemical Name:(1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde
CAS No.:758719-49-2
Molecular Formula:C₂₄H₃₀O₂Si
Molecular Weight:378.587
Hs Code.:

Synonyms:(1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

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Chemical Property of (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

Chemical Property:

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Technology Process of (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

There total 16 articles about (1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde 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: 93.0%

: 758719-49-2
(1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

Guidance literature:

Reference yield:

: [(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-methanol

: 758719-49-2
(1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1002/ejoc.200500289

Reference yield:

: 757240-15-6
(1R,5R)-5-Hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester

: 758719-49-2
(1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1.68 g / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

2.1: BH₃ / tetrahydrofuran / 2.5 h / 0 °C

2.2: 35 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

3.1: 81 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / 20 °C

4.1: 95 percent / K₂CO₃ / methanol / 6 h / 20 °C

5.1: 94 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

6.1: 71 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 45 - 50 °C

7.1: LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

8.1: NMO; TPAP / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-isopropyl azodicarboxylate; borane; potassium tert-butylate; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Mitsunobu inversion;
DOI:10.1002/ejoc.200500289