methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate

Base Information

Chemical Name:methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate
CAS No.:758719-59-4
Molecular Formula:C₂₅H₃₄O₄Si
Molecular Weight:426.628
Hs Code.:

Synonyms:methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate

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Chemical Property of methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate

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Technology Process of methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate

There total 5 articles about methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-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: 44.0%

: 326599-68-2
methyl (1S,5S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-3-cyclohexene-1-carboxylate

: 326599-69-3
methyl (1S,3S,4R,5S)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate

: 758719-59-4
methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate

Guidance literature:: methyl (1S,5S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-3-cyclohexene-1-carboxylate; With borane; In tetrahydrofuran; at 0 ℃; for 2.5h;

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; for 0.5h;
DOI:10.1002/ejoc.200500289

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 758719-59-4
methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

2.1: 98 percent / K₂CO₃ / methanol / 6 h / 20 °C

3.1: 91 percent / DIAD; PPh₃ / tetrahydrofuran / 3 h / 20 °C

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

4.2: 32 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

With 1H-imidazole; dmap; di-isopropyl azodicarboxylate; borane; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500289

Reference yield:

: 326598-95-2
(1R,3S,4S,5R)-5-acetoxy-3-hydroxy-4-methyl-1-(methoxycarbonyl)cyclohexane

: 758719-59-4
methyl (1S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)-5-hydroxy-4-methylcyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

2.1: 98 percent / K₂CO₃ / methanol / 6 h / 20 °C

3.1: 91 percent / DIAD; PPh₃ / tetrahydrofuran / 3 h / 20 °C

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

4.2: 32 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

With 1H-imidazole; dmap; di-isopropyl azodicarboxylate; borane; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500289