cyclo(N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe-N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe)

Base Information

• Chemical Name: cyclo(N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe-N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe)
• CAS No.: 312311-74-3
• Molecular Formula: C₄₄H₅₂N₄O₆
• Molecular Weight: 732.92
• Mol file: 312311-74-3.mol

Synonyms:cyclo(N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe-N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe)

Chemical Property of cyclo(N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe-N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclo(N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe-N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe)

There total 29 articles about cyclo(N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe-N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe) 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: 74.0%

cyclo(N-allyl-β3-hPhe-β3-hPhe-N-allyl-β3-hPhe-β3-hPhe) (223595-60-6) → cyclo(N-(2-hydroxyethyl)-β3-hPhe-β3-hPhe-N-(2-hydroxyethyl)-β3-hPhe-β3-hPhe) (312311-74-3)

Guidance literature:

cyclo(N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe); With ozone; In dichloromethane; at -78 ℃; for 0.666667h;

With sodium tetrahydroborate; In methanol; dichloromethane; at -20 ℃; for 0.666667h;

DOI:10.1016/S0040-4020(00)00666-9

Reference yield:

L-Phenylalaninol (3182-95-4) → cyclo(N-(2-hydroxyethyl)-β3-hPhe-β3-hPhe-N-(2-hydroxyethyl)-β3-hPhe-β3-hPhe) (312311-74-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: pyridine / CH₂Cl₂ / 10 h / 20 °C

1.2: 95 percent / KOH / H₂O

2.1: H₂O; acetonitrile / 16 h / 20 °C

3.1: 40.98 g / H₂O; HCl / acetic acid / 4 h / Heating

4.1: 90 percent / PTSA / 20 h / Heating

5.1: K₂CO₃ / dimethylformamide; H₂O / 18 h / 20 °C

6.1: 2.15 g / mercaptoacetic acid; DBU / dimethylformamide; H₂O / 3 h

7.1: 4.26 g / pyridine / tetrahydrofuran / 2 h / 20 °C

8.1: 88 percent / mercaptoacetic acid; DBU / dimethylformamide / 16 h

9.1: 75 percent / HOAt; EDC*HCl / CH₂Cl₂ / 20 h / 20 °C

10.1: 85 percent / DBU; mercaptoacetic acid / dimethylformamide / 23 h

11.1: LiOH; H₂O / methanol / 16 h

12.1: 254 mg / i-Pr₂NEt; HOAt; PyBroP / acetonitrile / 4 h / 70 °C

13.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

13.2: 74 percent / NaBH₄ / CH₂Cl₂; methanol / 0.67 h / -20 °C

With pyridine; hydrogenchloride; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; water; potassium carbonate; toluene-4-sulfonic acid; ozone; mercaptoacetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 1.2: Cyclization / 2.1: Addition / 3.1: Hydrolysis / 4.1: Esterification / 5.1: Alkylation / 6.1: Substitution / 7.1: Acylation / 8.1: Substitution / 9.1: Acylation / 10.1: Substitution / 11.1: Hydrolysis / 12.1: Cyclization / 13.1: Oxidation / 13.2: Reduction;

DOI:10.1016/S0040-4020(00)00666-9

Reference yield:

methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate (60398-42-7,142854-48-6) → cyclo(N-(2-hydroxyethyl)-β3-hPhe-β3-hPhe-N-(2-hydroxyethyl)-β3-hPhe-β3-hPhe) (312311-74-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 92 percent / LiOH; H₂O / dioxane / 20 h

2.1: 68 percent / i-Pr₂NEt; HOAt; PyBroP / CH₂Cl₂ / 16 h / 20 °C

3.1: 99 percent / LiOH; H₂O / dioxane / 23 h

4.1: EDC*HCl / CH₂Cl₂ / 15 h / 20 °C

5.1: CH₂Cl₂ / 2 h / 20 °C

6.1: 21 percent / i-Pr₂NEt / acetonitrile / 19 h / 70 °C

7.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

7.2: 74 percent / NaBH₄ / CH₂Cl₂; methanol / 0.67 h / -20 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; water; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In 1,4-dioxane; dichloromethane; acetonitrile; 1.1: Hydrolysis / 2.1: Acylation / 3.1: Hydrolysis / 4.1: Esterification / 5.1: carbamate cleavage / 6.1: Cyclization / 7.1: Oxidation / 7.2: Reduction;

DOI:10.1016/S0040-4020(00)00666-9

upstream raw materials:

cyclo(N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe)

L-Phenylalaninol

(S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid

methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate

Downstream raw materials:

cyclo(N-(2-azidoethyl)-β³-hPhe-β³-hPhe-N-(2-azidoethyl)-β³-hPhe-β³-hPhe)