(Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one

Base Information

• Chemical Name: (Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one
• CAS No.: 1329675-14-0
• Molecular Formula: C₃₈H₄₉NO₄S₂Si
• Molecular Weight: 676.029
• Mol file: 1329675-14-0.mol

Synonyms:(Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one

Chemical Property of (Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one

There total 7 articles about (Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-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: 95.0%

(3R,6S,Z)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-hydroxydec-4-en-1-one (1329675-13-9) + chloromethyl methyl ether (107-30-2) → (Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one (1329675-14-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/ejoc.201100510

Reference yield:

(4S)-1-(tetrahydro-2H-pyran-2-yloxy)oct-2-yn-4-ol (1329675-08-2) → (Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one (1329675-14-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 4 h

2.1: pyridinium p-toluenesulfonate / methanol / 5 h

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 5 h / 20 °C

4.1: hydrogen / dichloromethane / 10 h

5.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.42 h / 0 °C

5.2: 1 h / 0 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

With 1H-imidazole; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; dichloromethane; dimethyl sulfoxide; 5.1: Crimmins aldol reaction / 5.2: Crimmins aldol reaction;

DOI:10.1002/ejoc.201100510

Reference yield:

(4S)-4-{[(tert-butyl)diphenylsilyl]oxy}oct-2-ynal (1329675-11-7) → (Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one (1329675-14-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen / dichloromethane / 10 h

2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.42 h / 0 °C

2.2: 1 h / 0 °C

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

With hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; 2.1: Crimmins aldol reaction / 2.2: Crimmins aldol reaction;

DOI:10.1002/ejoc.201100510

upstream raw materials:

(4S)-1-(tetrahydro-2H-pyran-2-yloxy)oct-2-yn-4-ol

tert-butyldiphenyl[(4S)-1-(tetrahydro-2H-pyran-2-yloxy)oct-2-yn-4-yloxy]silane

(4S)-4-(tert-butyldiphenylsilyloxy)oct-2-yn-1-ol

(4S)-4-{[(tert-butyl)diphenylsilyl]oxy}oct-2-ynal

Downstream raw materials:

methyl (2Z,5R,6Z,8S)-8-(tert-butyldiphenylsilyloxy)-5-(methoxymethoxy)dodeca-2,6-dienoate