3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate

Base Information

• Chemical Name: 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate
• CAS No.: 1363373-47-0
• Molecular Formula: C₃₂H₃₂N₂O₇
• Molecular Weight: 556.615
• Mol file: 1363373-47-0.mol

Synonyms:3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate

Chemical Property of 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate

There total 15 articles about 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate 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: 97.0%

4-((4-aminophenyl)buta-1,3-diyn-1-yl)-N-((1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)benzamide (1363373-46-9) → 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate (1363373-47-0)

Guidance literature:

4-((4-aminophenyl)buta-1,3-diyn-1-yl)-N-((1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)benzamide; With water; acetic acid; In 1,4-dioxane; at 20 ℃; for 0.5h; Inert atmosphere;

With sodium hydrogencarbonate; In 1,4-dioxane; pH=10;

Reference yield:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate (1363373-47-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 36 h / 70 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

2.2: 0.5 h

3.1: dichloromethane / -78 °C / Inert atmosphere

3.2: 2.08 h / -78 °C / Inert atmosphere

3.3: 0.67 h / -78 - 0 °C

4.1: dichloromethane; diethyl ether / 0.03 h / -78 °C / Inert atmosphere; Cooling with ice

4.2: 0.25 h

5.1: dichloromethane / -78 °C / Inert atmosphere

5.2: 4.58 h / -78 °C / Inert atmosphere

5.3: 0.67 h / -78 - 0 °C

6.1: tetrahydrofuran / 1.55 h / 20 °C / Inert atmosphere; Cooling with ice

6.2: 0.25 h / pH 7

7.1: hydrogen / palladium 10% on activated carbon / methanol / 14 h / 20 °C

8.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 25 h / 0 - 20 °C / Inert atmosphere

9.1: water; acetic acid / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

9.2: pH 10

With boron trifluoride diethyl etherate; water; hydrogen; tetra-(n-butyl)ammonium iodide; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(S)-(3-methyloxetan-3-yl)methyl 2-(((benzyloxy)carbonyl)-amino)-3-hydroxypropanoate (206191-42-6) → 3-hydroxy-2-(hydroxymethyl)-2-methylpropyl (2S,3R)-2-(4-((4-aminophenyl)buta-1,3-diyn-1-yl)benzamido)-3-hydroxy-3-(4-hydroxyphenyl)butanoate (1363373-47-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

1.2: 0.5 h

2.1: dichloromethane / -78 °C / Inert atmosphere

2.2: 2.08 h / -78 °C / Inert atmosphere

2.3: 0.67 h / -78 - 0 °C

3.1: dichloromethane; diethyl ether / 0.03 h / -78 °C / Inert atmosphere; Cooling with ice

3.2: 0.25 h

4.1: dichloromethane / -78 °C / Inert atmosphere

4.2: 4.58 h / -78 °C / Inert atmosphere

4.3: 0.67 h / -78 - 0 °C

5.1: tetrahydrofuran / 1.55 h / 20 °C / Inert atmosphere; Cooling with ice

5.2: 0.25 h / pH 7

6.1: hydrogen / palladium 10% on activated carbon / methanol / 14 h / 20 °C

7.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 25 h / 0 - 20 °C / Inert atmosphere

8.1: water; acetic acid / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

8.2: pH 10

With boron trifluoride diethyl etherate; water; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

4-trimethylsilanylethynyl-benzoic acid methyl ester

methyl 4-iodobenzoate

3-hydroxymethyl-3-methyloxethane

Downstream raw materials:

4-((4-aminophenyl)buta-1,3-diyn-1-yl)-N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-3-(4-hydroxyphenyl)-1-oxobutan-2-yl)benzamide