(4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione

Base Information

• Chemical Name: (4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione
• CAS No.: 332902-42-8
• Molecular Formula: C₂₀H₂₇NO₂S₂
• Molecular Weight: 377.572
• Mol file: 332902-42-8.mol

Synonyms:(4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione

Chemical Property of (4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione

There total 3 articles about (4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione 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: 89.0%

(4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione (102831-92-5,487029-68-5) + α-methyl-trans-cinnamaldehyde dimethyl acetal (137032-32-7) → (4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione (332902-42-8)

Guidance literature:

(4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -83 - -50 ℃; for 2.58333h; Inert atmosphere;

α-methyl-trans-cinnamaldehyde dimethyl acetal; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2.08333h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/0471264229.os086.09

Reference yield:

(4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione (102831-92-5,487029-68-5) + α-methyl-trans-cinnamaldehyde dimethyl acetal (137032-32-7) → (4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione (332902-42-8) + (4S)-N-[(2R,3R,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione

Guidance literature:

(4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -40 ℃; for 2h;

α-methyl-trans-cinnamaldehyde dimethyl acetal; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2.5h; Further stages.;

DOI:10.1021/ol0070177

Reference yield:

α-methyl-trans-cinnamaldehyde (15174-47-7) → (4S)-N-[(2R,3S,4E)-2,4-dimethyl-3-methoxy-5-phenyl-4-pentenoyl]-4-isopropyl-1,3-thiazolidine-2-thione (332902-42-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Amberlyst 15 / methanol / 36 h / 20 °C / Inert atmosphere; Cooling with ice

2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2.58 h / -83 - -50 °C / Inert atmosphere

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

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1002/0471264229.os086.09

upstream raw materials:

(4S)-4-isopropyl-3-(1-oxopropyl)-1,3-thiazolidine-2-thione

α-methyl-trans-cinnamaldehyde dimethyl acetal

α-methyl-trans-cinnamaldehyde

Downstream raw materials:

(S)-4-isopropylthiazolidine-2-thione