ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-1-carboxylate

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Chemical Name:ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-1-carboxylate
CAS No.:198268-15-4
Molecular Formula:C₂₅H₄₀N₂O₄Si
Molecular Weight:460.689
Hs Code.:

Synonyms:ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-1-carboxylate

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Chemical Property of ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-1-carboxylate

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Technology Process of ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-1-carboxylate

There total 10 articles about ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-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%

: 305322-55-8
ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

: 198268-15-4
ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-1-carboxylate

Guidance literature:: With quinoline; hydrogen; Pd-BaSO₄; In methanol;
DOI:10.1021/jo971571l

Reference yield:

: 198268-10-9
(S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione

: 198268-15-4
ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: mol. sieves / hexane; CH₂Cl₂ / 90 h / 23 °C

1.2: 71 percent / AgOTf / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 °C

3.1: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: BuMgCl / tetrahydrofuran / 0.5 h / 0 - 23 °C

4.2: tetrahydrofuran / 1 h / 0 - 23 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5.2: 2.34 g / HCO₂NH₄; Bu₃P / [Pd₂(dba)3] / benzene / 48 h / 23 °C

6.1: 95 percent / quinoline; H₂ / Pd/BaSO₄ / methanol / 5 h / 23 °C

With quinoline; lithium aluminium tetrahydride; molecular sieve; oxalyl dichloride; hydrogen; butyl magnesium bromide; dimethyl sulfoxide; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Cycloaddition / 1.2: Isomerization / 2.1: Reduction / 3.1: Swern oxidation / 4.1: Metallation / 4.2: Grignard reaction / 5.1: mesylation / 5.2: Hydrogenolysis / 6.1: Catalytic hydrogenation;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5

Reference yield:

: 198268-22-3
ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

: 198268-15-4
ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{(Z)-5-[(tert-butyl)dimethylsilyloxy]but-2-enyl}-4,5-dihydropyrazole-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: BuMgCl / tetrahydrofuran / 0.5 h / 0 - 23 °C

2.2: tetrahydrofuran / 1 h / 0 - 23 °C

3.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 2.34 g / HCO₂NH₄; Bu₃P / [Pd₂(dba)3] / benzene / 48 h / 23 °C

4.1: 95 percent / quinoline; H₂ / Pd/BaSO₄ / methanol / 5 h / 23 °C

With quinoline; oxalyl dichloride; hydrogen; butyl magnesium bromide; dimethyl sulfoxide; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; dichloromethane; 1.1: Swern oxidation / 2.1: Metallation / 2.2: Grignard reaction / 3.1: mesylation / 3.2: Hydrogenolysis / 4.1: Catalytic hydrogenation;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5