(E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-diene-2,5,18-trione

Base Information

• Chemical Name: (E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-diene-2,5,18-trione
• CAS No.: 123186-91-4
• Molecular Formula: C₃₀H₃₉NO₆S
• Molecular Weight: 541.709

Synonyms:(E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-diene-2,5,18-trione

Chemical Property of (E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-diene-2,5,18-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-diene-2,5,18-trione

There total 13 articles about (E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-diene-2,5,18-trione 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:

(2E,4E)-4-methylhexa-2,4-dien-1-ol (70849-69-3,30338-90-0,57258-51-2) → (E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-diene-2,5,18-trione (123186-91-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 40 percent / BHT / xylene / 130 °C

2: 1.) KOH / 1.) H₂O, CH₃OH, C₆H₆, room temp., 2.) ether, CH₃OH

3: 100 percent / COCl₂, (C₂H₅)3N, DMSO / CH₂Cl₂ / -78 °C

4: 58 percent / tetrahydrofuran / -78 °C

5: 1.) n-C₄H₉Li / 1.) THF, HMPA, 0 deg C

6: 68 percent / PPTS / Ambient temperature

8: 1.) n-C₄H₉Li, DIBAL-H, 2.) PCC / 1.) THF, O deg C, 2.) CH₂Cl₂, room temp.

9: 2.) pyridine / 1.) THF, ether, -78 deg C, 2.) 0 deg C

10: 49 percent / 10percent (Ph₃P)4Pd, 10percent dppp / tetrahydrofuran / 1.) room temp., 2.) reflux

11: 1.) peracetic acid, K₂CO₃, 2.) PPTS / 1.) CH₂Cl₂, 2.) H₂O, THF, room temp.,

With pyridine; peracetic acid; potassium hydroxide; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; In tetrahydrofuran; dichloromethane; xylene;

DOI:10.1021/ja00203a042

Reference yield:

N-benzyloxycarbonyl-L-leucine methyl ester (51021-87-5) → (E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-diene-2,5,18-trione (123186-91-4)

Guidance literature:

Multi-step reaction with 12 steps

2: 40 percent / BHT / xylene / 130 °C

3: 1.) KOH / 1.) H₂O, CH₃OH, C₆H₆, room temp., 2.) ether, CH₃OH

4: 100 percent / COCl₂, (C₂H₅)3N, DMSO / CH₂Cl₂ / -78 °C

5: 58 percent / tetrahydrofuran / -78 °C

6: 1.) n-C₄H₉Li / 1.) THF, HMPA, 0 deg C

7: 68 percent / PPTS / Ambient temperature

9: 1.) n-C₄H₉Li, DIBAL-H, 2.) PCC / 1.) THF, O deg C, 2.) CH₂Cl₂, room temp.

10: 2.) pyridine / 1.) THF, ether, -78 deg C, 2.) 0 deg C

11: 49 percent / 10percent (Ph₃P)4Pd, 10percent dppp / tetrahydrofuran / 1.) room temp., 2.) reflux

12: 1.) peracetic acid, K₂CO₃, 2.) PPTS / 1.) CH₂Cl₂, 2.) H₂O, THF, room temp.,

With pyridine; peracetic acid; potassium hydroxide; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; In tetrahydrofuran; dichloromethane; xylene;

DOI:10.1021/ja00203a042

Reference yield:

methyl (3R,3aS,4R,7R,7aR)-7-hydroxymethyl-3-isobutyl-4,5-dimethyl-1-oxo-3a,4,7,7a-tetrahydroisoindoline-7a-carboxylate (86852-26-8) → (E)-(1S,3R,6S,11S,14S,15R,16S)-3-Benzenesulfonyl-6-hydroxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-diene-2,5,18-trione (123186-91-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / COCl₂, (C₂H₅)3N, DMSO / CH₂Cl₂ / -78 °C

2: 58 percent / tetrahydrofuran / -78 °C

3: 1.) n-C₄H₉Li / 1.) THF, HMPA, 0 deg C

4: 68 percent / PPTS / Ambient temperature

6: 1.) n-C₄H₉Li, DIBAL-H, 2.) PCC / 1.) THF, O deg C, 2.) CH₂Cl₂, room temp.

7: 2.) pyridine / 1.) THF, ether, -78 deg C, 2.) 0 deg C

8: 49 percent / 10percent (Ph₃P)4Pd, 10percent dppp / tetrahydrofuran / 1.) room temp., 2.) reflux

9: 1.) peracetic acid, K₂CO₃, 2.) PPTS / 1.) CH₂Cl₂, 2.) H₂O, THF, room temp.,

With pyridine; peracetic acid; n-butyllithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-bis-(diphenylphosphino)propane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00203a042

upstream raw materials:

(5Z,9E)-(1S,3R,11S,14S,15R,16S)-3-Benzenesulfonyl-5-ethoxy-16-isobutyl-9,13,14-trimethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-5,9,12-triene-2,18-dione

(2E,4E)-4-methylhexa-2,4-dien-1-ol

N-benzyloxycarbonyl-L-leucine methyl ester

methyl (3R,3aS,4R,7R,7aR)-7-hydroxymethyl-3-isobutyl-4,5-dimethyl-1-oxo-3a,4,7,7a-tetrahydroisoindoline-7a-carboxylate

Downstream raw materials:

(-)-Aspochalasin B

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