tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-1-carboxylate

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Chemical Name:tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-1-carboxylate
CAS No.:198268-23-4
Molecular Formula:C₂₁H₃₀N₂O₄
Molecular Weight:374.48
Hs Code.:

Synonyms:tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-1-carboxylate

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Chemical Property of tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-1-carboxylate

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Technology Process of tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-1-carboxylate

There total 13 articles about tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-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:

: 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

: 198268-23-4
tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-1-carboxylate

Guidance literature:: Multi-step reaction with 8 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

7.1: Ba(OH)2; H₂O / dioxane / 2 h / 100 °C

8.1: 1.43 g / NaOH / tetrahydrofuran; H₂O / 6 h / 23 °C

With quinoline; barium dihydroxide; sodium hydroxide; lithium aluminium tetrahydride; molecular sieve; oxalyl dichloride; water; hydrogen; butyl magnesium bromide; dimethyl sulfoxide; triethylamine; Pd-BaSO₄; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; 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 / 7.1: Decarboxylation / 8.1: Acylation;
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

: 198268-23-4
tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-1-carboxylate

Guidance literature:: Multi-step reaction with 6 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

5.1: Ba(OH)2; H₂O / dioxane / 2 h / 100 °C

6.1: 1.43 g / NaOH / tetrahydrofuran; H₂O / 6 h / 23 °C

With quinoline; barium dihydroxide; sodium hydroxide; oxalyl dichloride; water; hydrogen; butyl magnesium bromide; dimethyl sulfoxide; triethylamine; Pd-BaSO₄; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1.1: Swern oxidation / 2.1: Metallation / 2.2: Grignard reaction / 3.1: mesylation / 3.2: Hydrogenolysis / 4.1: Catalytic hydrogenation / 5.1: Decarboxylation / 6.1: Acylation;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5

Reference yield:

: 198268-13-2
ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-5-formyl-4,5-dihydropyrazole-1-carboxylate

: 198268-23-4
tert-butyl (4S,5S)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-[(Z)-5-hydroxypent-2-enyl]pyrazole-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

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

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

2.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 2.34 g / HCO₂NH₄; Bu₃P / [Pd₂(dba)3] / benzene / 48 h / 23 °C

3.1: 95 percent / quinoline; H₂ / Pd/BaSO₄ / methanol / 5 h / 23 °C

4.1: Ba(OH)2; H₂O / dioxane / 2 h / 100 °C

5.1: 1.43 g / NaOH / tetrahydrofuran; H₂O / 6 h / 23 °C

With quinoline; barium dihydroxide; sodium hydroxide; water; hydrogen; butyl magnesium bromide; triethylamine; Pd-BaSO₄; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1.1: Metallation / 1.2: Grignard reaction / 2.1: mesylation / 2.2: Hydrogenolysis / 3.1: Catalytic hydrogenation / 4.1: Decarboxylation / 5.1: Acylation;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5