Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide

Base Information

• Chemical Name: Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide
• CAS No.: 78443-16-0
• Molecular Formula: C₄₄H₅₉NO₈
• Molecular Weight: 729.954
• Mol file: 78443-16-0.mol

Synonyms:Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide

Chemical Property of Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide

There total 3 articles about Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide 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:

4-biphenyl-carboxylic acid chloride (14002-51-8) → Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide (78443-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: NaOH / H₂O; tetrahydrofuran; propan-2-ol / Ambient temperature

With dmap; sodium hydroxide; triethylamine; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol;

DOI:10.1021/ja00401a051

Reference yield:

(1S,2R,4R,5R,7R,9S,10R,13R,14R,15R,19S,20S)-13-Ethyl-4,14-dihydroxy-2,4,10,14,19,20-hexamethyl-7-(2,4,6-trimethyl-phenyl)-6,8,12,16-tetraoxa-18-aza-tricyclo[13.3.1.15,9]icosane-11,17-dione (78442-83-8) → Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide (78443-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: NaOH / H₂O; tetrahydrofuran; propan-2-ol / Ambient temperature

With dmap; sodium hydroxide; triethylamine; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol;

DOI:10.1021/ja00401a051

Reference yield:

(1S,2R,4R,5R,7R,9S,10R,13R,14R,15R,19S,20S)-18-(Biphenyl-4-carbonyl)-13-ethyl-4,14-dihydroxy-2,4,10,14,19,20-hexamethyl-7-(2,4,6-trimethyl-phenyl)-6,8,12,16-tetraoxa-18-aza-tricyclo[13.3.1.15,9]icosane-11,17-dione (78443-15-9) → Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide (78443-16-0) + (1S,2R,4R,5R,7R,9S,10R,13R,14R,15R,19S,20S)-13-Ethyl-4,14-dihydroxy-2,4,10,14,19,20-hexamethyl-7-(2,4,6-trimethyl-phenyl)-6,8,12,16-tetraoxa-18-aza-tricyclo[13.3.1.15,9]icosane-11,17-dione (78442-83-8)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; isopropyl alcohol; Yield given; Ambient temperature;

DOI:10.1021/ja00401a051

upstream raw materials:

(1S,2R,4R,5R,7R,9S,10R,13R,14R,15R,19S,20S)-18-(Biphenyl-4-carbonyl)-13-ethyl-4,14-dihydroxy-2,4,10,14,19,20-hexamethyl-7-(2,4,6-trimethyl-phenyl)-6,8,12,16-tetraoxa-18-aza-tricyclo[13.3.1.1^5,9]icosane-11,17-dione

4-biphenyl-carboxylic acid chloride

(1S,2R,4R,5R,7R,9S,10R,13R,14R,15R,19S,20S)-13-Ethyl-4,14-dihydroxy-2,4,10,14,19,20-hexamethyl-7-(2,4,6-trimethyl-phenyl)-6,8,12,16-tetraoxa-18-aza-tricyclo[13.3.1.1^5,9]icosane-11,17-dione

Downstream raw materials:

erythromycin

erythromycylamine

Biphenyl-4-carboxylic acid ((2R,3S,4R,5S,6S,7R,9R,10R,11S,12S,13R)-2-ethyl-3,4,9,10,12-pentahydroxy-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl)-amide