(2R,3S)-N,N-diallyl-3-cyclohexyl-3-hydroxy-2-methylpropanethioamide

Base Information

• Chemical Name: (2R,3S)-N,N-diallyl-3-cyclohexyl-3-hydroxy-2-methylpropanethioamide
• CAS No.: 1283722-11-1
• Molecular Formula: C₁₆H₂₇NOS
• Molecular Weight: 281.462
• Mol file: 1283722-11-1.mol

Synonyms:

Chemical Property of (2R,3S)-N,N-diallyl-3-cyclohexyl-3-hydroxy-2-methylpropanethioamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-N,N-diallyl-3-cyclohexyl-3-hydroxy-2-methylpropanethioamide

There total 5 articles about (2R,3S)-N,N-diallyl-3-cyclohexyl-3-hydroxy-2-methylpropanethioamide 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:

N,N-(diallyl)thiopropionamide (1283722-06-4) + cyclohexanecarbaldehyde (2043-61-0) → C16H27NOS + (2R,3S)-N,N-diallyl-3-cyclohexyl-3-hydroxy-2-methylpropanethioamide (1283722-11-1)

Guidance literature:

With n-butyllithium; 2,2,5,7,8-pentamethylchroman-6-ol; Cu(MeCN)4*PF₆; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; In tetrahydrofuran; hexane; at -70 ℃; for 40h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja200250p

Reference yield:

N,N-(diallyl)thiopropionamide (1283722-06-4) + cyclohexanecarbaldehyde (2043-61-0) → (2R,3S)-N,N-diallyl-3-cyclohexyl-3-hydroxy-2-methylpropanethioamide (1283722-11-1) + C16H27NOS + C16H27NOS

Guidance literature:

With C₅H₁₁NOS; C₉H₁₁^(1-)*Cu⁽¹⁺⁾*C₃₄H₃₆P₂*C₁₄H₂₀O₂; In tetrahydrofuran; at -70 ℃; for 48h; Overall yield = 95 %Spectr.; enantioselective reaction;

DOI:10.1039/c5sc02218e

Reference yield:

N,N-diallylpropanamide (25243-23-6) → C16H27NOS + (2R,3S)-N,N-diallyl-3-cyclohexyl-3-hydroxy-2-methylpropanethioamide (1283722-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Lawessons reagent / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

2: Cu(MeCN)4*PF₆; n-butyllithium; 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane / tetrahydrofuran; hexane / 40 h / -70 °C / Inert atmosphere

With Lawessons reagent; n-butyllithium; 2,2,5,7,8-pentamethylchroman-6-ol; Cu(MeCN)4*PF₆; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; In tetrahydrofuran; hexane;

DOI:10.1021/ja200250p

upstream raw materials:

N,N-(diallyl)thiopropionamide

cyclohexanecarbaldehyde

N,N-diallylpropanamide

diallylamine

Refernces

• 1、 Iwata, Mitsutaka,Yazaki, Ryo,Chen, I-Hon,Sureshkumar, Devarajulu,Kumagai, Naoya,Shibasaki, Masakatsu. "Direct catalytic enantio- and diastereoselective aldol reaction of thioamides". supporting information; experimental part. p. 5554 - 5560. Retrieved 2011/05/14.