(3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one

Base Information

• Chemical Name: (3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one
• CAS No.: 1266664-10-1
• Molecular Formula: C₂₆H₃₁NO₃S₂
• Molecular Weight: 469.669
• Mol file: 1266664-10-1.mol

Synonyms:(3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one

Chemical Property of (3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one

There total 6 articles about (3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one 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:

1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone (911040-42-1) + (S)-3-(benzyloxy)-2,2-dimethylpent-4-enal (570371-48-1) → (3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one (1266664-10-1) + (3R,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one

Guidance literature:

1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.333333h; Inert atmosphere;

(S)-3-(benzyloxy)-2,2-dimethylpent-4-enal; In dichloromethane; at -78 ℃; for 0.166667h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo102401v

Reference yield:

(R)-Pantolacton (599-04-2) → (3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one (1266664-10-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: boron trifluoride diethyl etherate / dichloromethane; cyclohexane / 48 h / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: pyridinium chlorochromate / dichloromethane / 8 h / 20 °C / Inert atmosphere

5.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

5.2: 0.17 h / -78 °C / Inert atmosphere

With boron trifluoride diethyl etherate; potassium tert-butylate; titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; cyclohexane; toluene; 3.1: Wittig reaction / 5.1: Crimmin's acetate aldol reaction / 5.2: Crimmin's acetate aldol reaction;

DOI:10.1021/jo102401v

Reference yield:

(R)-2-Benzyloxy-4-hydroxy-3,3-dimethyl-butyraldehyde → (3S,5S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-4,4-dimethylhept-6-en-1-one (1266664-10-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: pyridinium chlorochromate / dichloromethane / 8 h / 20 °C / Inert atmosphere

3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

3.2: 0.17 h / -78 °C / Inert atmosphere

With potassium tert-butylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 1.1: Wittig reaction / 3.1: Crimmin's acetate aldol reaction / 3.2: Crimmin's acetate aldol reaction;

DOI:10.1021/jo102401v

upstream raw materials:

1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone

(S)-3-(benzyloxy)-2,2-dimethylpent-4-enal

benzimidate

(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

Downstream raw materials:

(3S,5S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,4,4-trimethylhept-6-enamide