(E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

Base Information

Chemical Name:(E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester
CAS No.:519002-51-8
Molecular Formula:C₄₁H₆₈N₄O₆Si
Molecular Weight:741.1
Hs Code.:

(E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

Synonyms:(E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

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Chemical Property of (E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

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Technology Process of (E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

There total 7 articles about (E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester 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:

: 104372-55-6,519002-37-0
(S)-(E)-2-methyl-hex-4-enal

: 519002-51-8
(E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Et₃N; dibutylboron triflate / CH₂Cl₂ / 0.75 h / 0 °C

1.2: CH₂Cl₂ / 5 h / -78 °C

1.3: 92 percent / aq. H₂O₂ / CH₂Cl₂; methanol / 0.67 h / -78 - 0 °C

2.1: 76 percent / aq. H₂O₂; aq. LiOH / tetrahydrofuran / 2 h / 0 °C

3.1: 890 mg / N-methylmorpholine; EDC; HOBT / CH₂Cl₂ / 20 °C

4.1: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

5.1: 362 mg / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 20 °C

6.1: 88 percent / pyridine / CH₂Cl₂ / 4 h / 0 °C

With 4-methyl-morpholine; pyridine; lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 5.1: Mitsunobu reaction;
DOI:10.1021/ja021327y

Reference yield:

: (S)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-phenyl-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester

: 519002-51-8
(E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 890 mg / N-methylmorpholine; EDC; HOBT / CH₂Cl₂ / 20 °C

2: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

3: 362 mg / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 20 °C

4: 88 percent / pyridine / CH₂Cl₂ / 4 h / 0 °C

With 4-methyl-morpholine; pyridine; lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 3: Mitsunobu reaction;
DOI:10.1021/ja021327y

Reference yield:

: 247186-16-9
(tert-butoxycarbonyl)-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic asid methyl ester

: 519002-51-8
(E)-(2R,3S,4S)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-oct-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: TFA / CH₂Cl₂ / 2 h / 0 °C

2: 890 mg / N-methylmorpholine; EDC; HOBT / CH₂Cl₂ / 20 °C

3: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

4: 362 mg / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 20 °C

5: 88 percent / pyridine / CH₂Cl₂ / 4 h / 0 °C

With 4-methyl-morpholine; pyridine; lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 4: Mitsunobu reaction;
DOI:10.1021/ja021327y