(S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: (S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 907602-59-9
• Molecular Formula: C₅₁H₆₈BrN₃O₇Si
• Molecular Weight: 943.106

Synonyms:(S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property of (S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property:

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Technology Process of (S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl ester

There total 6 articles about (S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl 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: 81.0%

2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylamine (907602-52-2) + Fmoc-(S)-β3-HLys(Boc)-OH (203854-47-1) → (S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl ester (907602-59-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jm050708u

Reference yield:

5-(2-aminoethyl)-2-benzyloxy-3-bromophenol (907602-39-5) → (S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl ester (907602-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetonitrile / 3 h

1.2: 76 percent / Na₂CO₃ / methanol; H₂O / 12 h / 20 °C

2.1: 95 percent / imidazole / dimethylformamide / 20 °C

3.1: 95 percent / CF₃CO₂H / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 81 percent / HOBt; EDCI / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm050708u

Reference yield:

[2-(4-benzyloxy-3-bromo-5-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester (907602-50-0) → (S)-(-)-(6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-tert-butoxycarbonylamino-hexyl)carbamic acid 9H-fluoren-9-ylmethyl ester (907602-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / imidazole / dimethylformamide / 20 °C

2: 95 percent / CF₃CO₂H / CH₂Cl₂ / 0.5 h / 0 °C

3: 81 percent / HOBt; EDCI / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050708u

upstream raw materials:

2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylamine

Fmoc-(S)-β³-HLys(Boc)-OH

5-(2-aminoethyl)-2-benzyloxy-3-bromophenol

[2-(4-benzyloxy-3-bromo-5-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester

Downstream raw materials:

(S)-[4-(20-amino-4-benzyloxy-5-bromo-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester

(S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester

(S)-(-)-{6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-[3-(4-fluoro-3-nitrophenyl)propionylamino]hexyl}carbamic acid tert-butyl ester

{5-amino-6-[2-(4-benzyloxy-3-bromo-5-triisopropylsilanyloxy-phenyl)-ethylcarbamoyl]-hexyl}-carbamic acid tert-butyl ester

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