14-O-{[4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin

Base Information

• Chemical Name: 14-O-{[4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin
• CAS No.: 1061660-17-0
• Molecular Formula: C₃₃H₅₃NO₇S
• Molecular Weight: 607.852
• Mol file: 1061660-17-0.mol

Synonyms:14-O-{[4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin

Chemical Property of 14-O-{[4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 14-O-{[4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin

There total 4 articles about 14-O-{[4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin 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: 43.0%

14-O-[(mercapto)acetyl]mutilin (70004-29-4) + (1R,3R,6S)-(7-oxabicyclo[4.1.0]hept-3-yl)carbamic acid tert-butyl ester (1350636-88-2) → 14-O-{[4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin (1061660-17-0) + 14-O-{[5-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin

Guidance literature:

14-O-[(mercapto)acetyl]mutilin; With DBN; at 20 ℃; for 1h; Inert atmosphere;

(1R,3R,6S)-(7-oxabicyclo[4.1.0]hept-3-yl)carbamic acid tert-butyl ester; at 20 ℃; for 16h; Product distribution / selectivity; Inert atmosphere;

Reference yield:

pleuromutilin tosylate (31716-01-5) + tert-butyl [3-hydroxy-4-mercapto-cyclohexyI]-carbamate → 14-O-{[(1RS,2RS,4RS)-4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin (1061660-17-0)

Guidance literature:

With sodium hydroxide; benzyltri(n-butyl)ammonium chloride; In tert-butyl methyl ether; water; at 20 - 25 ℃; for 1h; Inert atmosphere;

Reference yield:

pleuromutilin → 14-O-{[(1RS,2RS,4RS)-4-tert-butoxycarbonylamino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin (1061660-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / dichloromethane / 20.33 h / 10 - 25 °C / Reflux; Industry scale

2: sodium hydroxide / benzyltri(n-butyl)ammonium chloride / water; tert-butyl methyl ether / 1 h / 20 - 25 °C / Inert atmosphere

With sodium hydroxide; benzyltri(n-butyl)ammonium chloride; In dichloromethane; tert-butyl methyl ether; water;

upstream raw materials:

pleuromutilin tosylate

14-O-[(mercapto)acetyl]mutilin

(1R,3R,6S)-(7-oxabicyclo[4.1.0]hept-3-yl)carbamic acid tert-butyl ester

Downstream raw materials:

lefamulin acetate

14-O-{[(1R,2R,4R)-4-amino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin L-lactate

14-O-{[(1R,2R,4R)-4-amino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin hydrogenmaleate

14-O-{[(1R,2R,4R)-4-ethoxycarbonylamino-2-hydroxy-cyclohexyl-sulfanyl]-acetyl}-mutilin