(4S,11S,14S,17S)-4,11,17-Triisopropyl-14-((R)-1-trityloxy-ethyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1⁽²⁰⁾,5⁽²²⁾,7,18⁽²¹⁾-tetraene-2,9,12,15-tetraone

Base Information

• Chemical Name: (4S,11S,14S,17S)-4,11,17-Triisopropyl-14-((R)-1-trityloxy-ethyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1⁽²⁰⁾,5⁽²²⁾,7,18⁽²¹⁾-tetraene-2,9,12,15-tetraone
• CAS No.: 831239-07-7
• Molecular Formula: C₄₄H₅₀N₆O₆S
• Molecular Weight: 790.984

Synonyms:

Chemical Property of (4S,11S,14S,17S)-4,11,17-Triisopropyl-14-((R)-1-trityloxy-ethyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1⁽²⁰⁾,5⁽²²⁾,7,18⁽²¹⁾-tetraene-2,9,12,15-tetraone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (4S,11S,14S,17S)-4,11,17-Triisopropyl-14-((R)-1-trityloxy-ethyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1⁽²⁰⁾,5⁽²²⁾,7,18⁽²¹⁾-tetraene-2,9,12,15-tetraone

There total 11 articles about (4S,11S,14S,17S)-4,11,17-Triisopropyl-14-((R)-1-trityloxy-ethyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1⁽²⁰⁾,5⁽²²⁾,7,18⁽²¹⁾-tetraene-2,9,12,15-tetraone 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:

2-{(S)-1-[(2-{(S)-1-[(2S,3R)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-trityloxy-butyrylamino]-2-methyl-propyl}-oxazole-4-carbonyl)-amino]-2-methyl-propyl}-thiazole-4-carboxylic acid → (4S,11S,14S,17S)-4,11,17-Triisopropyl-14-((R)-1-trityloxy-ethyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.15,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetraone (831239-07-7)

Guidance literature:

With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; for 10h;

DOI:10.1016/j.tet.2004.10.024

Reference yield:

Fmoc-Val-OH (68858-20-8) → (4S,11S,14S,17S)-4,11,17-Triisopropyl-14-((R)-1-trityloxy-ethyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.15,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetraone (831239-07-7)

Guidance literature:

Multi-step reaction with 12 steps

1: HBTU; HOBt; DIEA

2: 89 percent / Ph₃PO; Tf₂O / CH₂Cl₂ / -20 °C

3: 94 percent / MnO₂

4: diethylamine / acetonitrile / 0.5 h / 25 °C

5: 88 percent / HBTU; HOBt*H₂O; N,N-diisopropylethylamine / dimethylformamide / 8 h / 25 °C

6: TFA / CH₂Cl₂ / 0.33 h

7: HBTU; HOBt*H₂O; N,N-diisopropylethylamine / dimethylformamide / 8 h / 25 °C

8: diethylamine / acetonitrile / 0.5 h / 25 °C

9: HBTU; HOBt*H₂O; N,N-diisopropylethylamine / dimethylformamide / 8 h / 25 °C

10: diethylamine / acetonitrile / 0.5 h / 25 °C

11: Pd(OAc)2; polystyrene-triphenylphosphine; Ph₃SiH / CH₂Cl₂ / 0.25 h

12: PyBOP; DMAP / CH₂Cl₂; dimethylformamide / 10 h

With dmap; manganese(IV) oxide; palladium diacetate; polystyrene-triphenylphosphine; trifluoromethylsulfonic anhydride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; Triphenylphosphine oxide; HSiPh₃; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2004.10.024

Reference yield:

allyl (S)-2-(1-amino-2-methylpropyl)thiazole-4-carboxylate (668489-42-7) → (4S,11S,14S,17S)-4,11,17-Triisopropyl-14-((R)-1-trityloxy-ethyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.15,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetraone (831239-07-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / HBTU; HOBt*H₂O; N,N-diisopropylethylamine / dimethylformamide / 8 h / 25 °C

2: TFA / CH₂Cl₂ / 0.33 h

3: HBTU; HOBt*H₂O; N,N-diisopropylethylamine / dimethylformamide / 8 h / 25 °C

4: diethylamine / acetonitrile / 0.5 h / 25 °C

5: HBTU; HOBt*H₂O; N,N-diisopropylethylamine / dimethylformamide / 8 h / 25 °C

6: diethylamine / acetonitrile / 0.5 h / 25 °C

7: Pd(OAc)2; polystyrene-triphenylphosphine; Ph₃SiH / CH₂Cl₂ / 0.25 h

8: PyBOP; DMAP / CH₂Cl₂; dimethylformamide / 10 h

With dmap; palladium diacetate; polystyrene-triphenylphosphine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; HSiPh₃; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2004.10.024

upstream raw materials:

Fmoc-Val-OH

allyl (S)-2-(1-amino-2-methylpropyl)thiazole-4-carboxylate

2-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-propyl]-thiazole-4-carboxylic acid allyl ester

(R)-2-[(S)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propyl]-4,5-dihydro-thiazole-4-carboxylic acid allyl ester

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