(R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione

Base Information

• Chemical Name: (R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione
• CAS No.: 1384192-99-7
• Molecular Formula: C₂₉H₃₉NO₃S₂Si
• Molecular Weight: 541.851

Synonyms:(R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione

Chemical Property of (R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione

There total 4 articles about (R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-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:

(3R,4E)-3-(tert-butyldimethylsilanyloxy)-5-phenylpent-4-enal (917251-11-7) + 1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone (911040-42-1) → (R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione (1384192-99-7) + (R)-4-benzyl-3-[(3S,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione (1384193-08-1)

Guidance literature:

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

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

(3R,4E)-3-(tert-butyldimethylsilanyloxy)-5-phenylpent-4-enal; In dichloromethane; at -78 ℃; for 0.25h; optical yield given as %de; Inert atmosphere;

DOI:10.1055/s-0031-1290771

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → (R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione (1384192-99-7) + (R)-4-benzyl-3-[(3S,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione (1384193-08-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium tetrachloride / dichloromethane / 0 °C / Inert atmosphere

1.2: 0.17 h / 0 °C / Inert atmosphere

1.3: 0.17 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.17 h / -78 °C / Inert atmosphere

4.1: titanium tetrachloride / dichloromethane / 0 °C / Inert atmosphere

4.2: 0.17 h / 0 °C / Inert atmosphere

4.3: 0.25 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium tetrachloride; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1055/s-0031-1290771

Reference yield:

(4S)-4-benzyl-3-[(3R,4E)-3-hydroxy-5-phenylpent-4-enoyl]-1,3-thiazolidine-2-thione (1384193-00-3) → (R)-4-benzyl-3-[(3R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione (1384192-99-7) + (R)-4-benzyl-3-[(3S,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-7-phenylhept-6-enoyl]-1,3-thiazolidine-2-thione (1384193-08-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.17 h / -78 °C / Inert atmosphere

3.1: titanium tetrachloride / dichloromethane / 0 °C / Inert atmosphere

3.2: 0.17 h / 0 °C / Inert atmosphere

3.3: 0.25 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium tetrachloride; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1055/s-0031-1290771

upstream raw materials:

(3R,4E)-3-(tert-butyldimethylsilanyloxy)-5-phenylpent-4-enal

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

(E)-3-phenylpropenal

(4S)-4-benzyl-3-[(3R,4E)-3-hydroxy-5-phenylpent-4-enoyl]-1,3-thiazolidine-2-thione

Downstream raw materials:

(3R,5R,6E)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-7-phenylhept-6-enal

(2E,8E)-(5S,7R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-phenyl-nona-2,8-dienal

(R)-6-[(1E,4S,6R,7E)-4,6-bis{[tert-butyl(dimethyl)silyl]oxy}-8-phenylocta-1,7-dien-1-yl]-5,6-dihydro-2H-pyran-2-one

(4R,6S,8R,9E)-6,8-bis{[tert-butyl(dimethyl)silyl]oxy}-10-phenyldeca-1,9-dien-4-ol

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