methyl N-tert-butoxycarbonyl-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate

Base Information

• Chemical Name: methyl N-tert-butoxycarbonyl-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate
• CAS No.: 223595-66-2
• Molecular Formula: C₂₉H₃₈N₂O₅
• Molecular Weight: 494.631

Synonyms:methyl N-tert-butoxycarbonyl-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate

Chemical Property of methyl N-tert-butoxycarbonyl-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate

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Technology Process of methyl N-tert-butoxycarbonyl-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate

There total 9 articles about methyl N-tert-butoxycarbonyl-(S)-β³-homophenylalanyl-N-allyl-(S)-β³-homophenylalaninate 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: 68.0%

(S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid (51871-62-6) + methyl (S)-3-allylamino-4-phenylbutanoate hydrochloride → methyl N-tert-butoxycarbonyl-(S)-β3-homophenylalanyl-N-allyl-(S)-β3-homophenylalaninate (223595-66-2)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; for 16h;

DOI:10.1016/S0040-4039(99)00234-8

Reference yield:

methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate (60398-42-7,142854-48-6) → methyl N-tert-butoxycarbonyl-(S)-β3-homophenylalanyl-N-allyl-(S)-β3-homophenylalaninate (223595-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / LiOH; H₂O / dioxane / 20 h

2: 68 percent / i-Pr₂NEt; HOAt; PyBroP / CH₂Cl₂ / 16 h / 20 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; water; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In 1,4-dioxane; dichloromethane; 1: Hydrolysis / 2: Acylation;

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

Reference yield:

L-Phenylalaninol (3182-95-4) → methyl N-tert-butoxycarbonyl-(S)-β3-homophenylalanyl-N-allyl-(S)-β3-homophenylalaninate (223595-66-2)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran; H₂O / 17 h

2: pyridine / CHCl₃ / 22 h

3: H₂O₂, NaOH / methanol; H₂O / 2 h

4: (MeO)2CHNMe₂

5: KHMDS / dimethylformamide / 0.5 h / -20 °C

6: TFA / CH₂Cl₂ / 0.5 h

7: 68 percent / PyBroP, HOAt, Et-i-Pr₂N / CH₂Cl₂ / 16 h

With pyridine; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; dihydrogen peroxide; potassium hexamethylsilazane; N,N-dimethyl-formamide dimethyl acetal; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00234-8

upstream raw materials:

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

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

(S)-3-<(tert-butoxycarbonyl)amino>-4-phenylbutanenitrile

(S)-3-tert-butoxycarbonylamino-4-phenylbutanamide

Downstream raw materials:

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

Boc-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-OMe

Boc-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-OH

H-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-OC6F5

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