(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

Base Information

Chemical Name:(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene
CAS No.:497067-24-0
Molecular Formula:C₂₀H₃₅NO₃Si
Molecular Weight:365.588
Hs Code.:

Synonyms:(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

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Chemical Property of (3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

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Technology Process of (3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

There total 6 articles about (3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene 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: 92.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 497067-20-6
(3S,5R)-3-[(tert-butoxycarbonyl)amino]-1-ethynyl-5-hydroxy-2-methylcyclohex-1-ene

: 497067-24-0
(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo026474t

Reference yield:

: 115540-15-3
(1S,5R)-5-acetoxy-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene

: 497067-24-0
(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

2: 56 percent / Mg; MeOH / 6 h / -30 °C

3: 83 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 5.5 h / 20 °C

4: MeNH₂ / ethanol / 36 h / 20 - 65 °C

5: 117 mg / NaHCO₃ / CHCl₃; H₂O / 24 h / 20 °C

6: 92 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; methanol; sodium hydrogencarbonate; magnesium; triphenylphosphine; methylamine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water;
DOI:10.1021/jo026474t

Reference yield:

: 350985-91-0
(3R,5R)-5-acetoxy-1-ethynyl-2-methyl-3-[(4-nitrophenyl)carbonyloxy]cyclohex-1-ene

: 497067-24-0
(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 56 percent / Mg; MeOH / 6 h / -30 °C

2: 83 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 5.5 h / 20 °C

3: MeNH₂ / ethanol / 36 h / 20 - 65 °C

4: 117 mg / NaHCO₃ / CHCl₃; H₂O / 24 h / 20 °C

5: 92 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; methanol; sodium hydrogencarbonate; magnesium; triphenylphosphine; methylamine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water;
DOI:10.1021/jo026474t