4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol

Base Information

• Chemical Name: 4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol
• CAS No.: 1363373-45-8
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335
• Mol file: 1363373-45-8.mol

Synonyms:4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol

Chemical Property of 4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol

There total 8 articles about 4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol 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: 99.0%

benzyl ((1S,2R)-2-(4-(benzyloxy)phenyl)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)carbamate (1363373-44-7) → 4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol (1363373-45-8)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 20 ℃; for 14h;

Reference yield:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → 4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol (1363373-45-8)

Guidance literature:

Multi-step reaction with 7 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

With boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

1-[N-benzyloxycarbonyl-(1S)-1-amino-2-hydroxyethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (206191-44-8,851974-77-1) → 4-((1S,2R)-1-amino-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propan-2-yl)phenol (1363373-45-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dichloromethane / -78 °C / Inert atmosphere

1.2: 2.08 h / -78 °C / Inert atmosphere

1.3: 0.67 h / -78 - 0 °C

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

2.2: 0.25 h

3.1: dichloromethane / -78 °C / Inert atmosphere

3.2: 4.58 h / -78 °C / Inert atmosphere

3.3: 0.67 h / -78 - 0 °C

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

4.2: 0.25 h / pH 7

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

With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

upstream raw materials:

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

3-hydroxymethyl-3-methyloxethane

(S)-(3-methyloxetan-3-yl)methyl 2-(((benzyloxy)carbonyl)-amino)-3-hydroxypropanoate

1-[N-benzyloxycarbonyl-(1S)-1-amino-2-hydroxyethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

Downstream raw materials:

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

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

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