(6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaene-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaene-2-carboxylic acid tert-butyl ester
• CAS No.: 130408-39-8
• Molecular Formula: C₅₁H₇₄N₂O₁₃
• Molecular Weight: 923.154
• Mol file: 130408-39-8.mol

Synonyms:(6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaene-2-carboxylic acid tert-butyl ester

Chemical Property of (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaene-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaene-2-carboxylic acid tert-butyl ester

There total 11 articles about (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaene-2-carboxylic acid tert-butyl 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: 88.0%

di-tert-butyl dicarbonate (24424-99-5) + (+)-trienomycin A (98873-83-7) → (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24),21-heptaene-2-carboxylic acid tert-butyl ester (130408-39-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1021/ja00176a070 DOI:10.1021/ja961400i

Reference yield:

(+)-trienomycinol (117543-72-3) → (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24),21-heptaene-2-carboxylic acid tert-butyl ester (130408-39-8)

Guidance literature:

Multi-step reaction with 8 steps

1: CSA

2: 71 percent / i-Pr₂EtN / CH₂Cl₂

3: 95 percent / camphorosulfonic acid / methanol

4: 56 percent / DMAP / CH₂Cl₂ / -78 °C

5: Et₂NH / CH₂Cl₂ / 0.5 h / 25 °C

6: benzotriazol-1-yloxytris(dimethylamino phosphonium hexafluorophosphate (BOP), Et₃N / CH₂Cl₂

7: 86 percent / TBAF / methanol; tetrahydrofuran

8: 88 percent / DMAP, Et₃N / CH₂Cl₂

With dmap; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja961400i

Reference yield:

(+)-trienomycin C (100662-00-8) → (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15,22-Bis-tert-butoxycarbonyloxy-13-[(R)-2-(cyclohexanecarbonyl-amino)-propionyloxy]-5-methoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24),21-heptaene-2-carboxylic acid tert-butyl ester (130408-39-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 77 percent / aq. KOH / tetrahydrofuran

2: CSA

3: 71 percent / i-Pr₂EtN / CH₂Cl₂

4: 95 percent / camphorosulfonic acid / methanol

5: 56 percent / DMAP / CH₂Cl₂ / -78 °C

6: Et₂NH / CH₂Cl₂ / 0.5 h / 25 °C

7: benzotriazol-1-yloxytris(dimethylamino phosphonium hexafluorophosphate (BOP), Et₃N / CH₂Cl₂

8: 86 percent / TBAF / methanol; tetrahydrofuran

9: 88 percent / DMAP, Et₃N / CH₂Cl₂

With dmap; potassium hydroxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja961400i

upstream raw materials:

di-tert-butyl dicarbonate

(+)-trienomycin A

(+)-trienomycinol

(+)-trienomycin C