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

Base Information

Chemical Name:(1S,3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate
CAS No.:758719-44-7
Molecular Formula:C₂₄H₃₀O₂Si
Molecular Weight:378.587
Hs Code.:

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

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

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

There total 8 articles about (1S,3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate 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: 95.0%

: 758719-79-8
[(1S,3R,4S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-methanol

: 758719-44-7
(1S,3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate

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

: 758719-44-7
(1S,3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

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

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

2.2: 45 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

3.1: 95 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

4.1: 70 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 45 - 50 °C

5.1: 97 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

6.1: 95 percent / NMO; TPAP / CH₂Cl₂ / 0.5 h / 20 °C

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

Reference yield:

: 758719-38-9
methyl (1R,5R)-5-(tert-butyldiphenylsilyloxy)-4-methyl-3-cyclohexene-1-carboxylate

: 758719-44-7
(1S,3R,4S,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 45 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

2.1: 95 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

3.1: 70 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 45 - 50 °C

4.1: 97 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

5.1: 95 percent / NMO; TPAP / CH₂Cl₂ / 0.5 h / 20 °C

With lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane; potassium tert-butylate; triethylamine; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1002/ejoc.200500289