(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

Base Information

• Chemical Name: (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
• CAS No.: 78442-83-8
• Molecular Formula: C₃₂H₄₉NO₈
• Molecular Weight: 575.743
• Mol file: 78442-83-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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: 70.0%

(R)-2-[(2R,4S,5S,6R)-6-{(1R,3R)-3-[(4S,5S,6R)-6-((1R,2R)-1,2-Dihydroxy-1-methyl-butyl)-5-methyl-2-oxo-[1,3]oxazinan-4-yl]-1-hydroxy-1-methyl-butyl}-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-thiopropionic acid S-pyridin-2-yl ester (78442-97-4) → (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:

In toluene; at 110 ℃;

DOI:10.1021/ja00401a050

Reference yield:

(R)-2-[(2R,4S,5S,6R)-6-{(1R,3R)-3-[(4S,5S,6R)-6-((1R,2R)-1,2-Dihydroxy-1-methyl-butyl)-5-methyl-2-oxo-[1,3]oxazinan-4-yl]-1-hydroxy-1-methyl-butyl}-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-propionic acid → (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:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: 70 percent / toluene / 110 °C

With triethylamine; In dichloromethane; toluene;

DOI:10.1021/ja00401a050

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:

4-Nitrophenyl chloroformate

(R)-2-[(2R,4S,5S,6R)-6-{(1R,3R)-3-[(4S,5S,6R)-6-((1R,2R)-1,2-Dihydroxy-1-methyl-butyl)-5-methyl-2-oxo-[1,3]oxazinan-4-yl]-1-hydroxy-1-methyl-butyl}-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-thiopropionic acid S-pyridin-2-yl ester

(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

Downstream 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

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

(R)-2-[(2R,4S,5S,6R)-6-{(1R,3R)-3-[(4S,5S,6R)-6-((1R,2R)-1,2-Dihydroxy-1-methyl-butyl)-5-methyl-2-oxo-[1,3]oxazinan-4-yl]-1-hydroxy-1-methyl-butyl}-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-thiopropionic acid S-pyridin-2-yl ester