(2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid

Base Information

• Chemical Name: (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid
• CAS No.: 139944-50-6
• Molecular Formula: C₃₇H₅₇NO₇SSi
• Molecular Weight: 688.014
• Mol file: 139944-50-6.mol

Synonyms:(2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid

Chemical Property of (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid

There total 6 articles about (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid 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:

(S)-4-{(2R,4S,6R)-4-Hydroxy-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-hydroxy-1-methyl-propyl ester (140146-97-0) → (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid (139944-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

2: 96.7 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C

3: 1.) DMSO, pyridine, CF₃COOH, 2.) dicyclohexylcarbodiimide / 1.) benzene, RT, 15 min, 2.) benzene, RT, 6 h

4: 1.) hexamethylphosphoric triamide (HMPA), potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, toluene, -78 deg C, 1 h

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; potassium hexamethylsilazane; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ja00034a036

Reference yield:

(S)-4-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester (140146-99-2) → (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid (139944-50-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 96.7 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C

2: 1.) DMSO, pyridine, CF₃COOH, 2.) dicyclohexylcarbodiimide / 1.) benzene, RT, 15 min, 2.) benzene, RT, 6 h

3: 1.) hexamethylphosphoric triamide (HMPA), potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, toluene, -78 deg C, 1 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; potassium hexamethylsilazane; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja00034a036

Reference yield:

(S)-4-{(2R,4S,6R)-4,6-Dihydroxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-hydroxy-1-methyl-propyl ester (139944-42-6) → (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-3,10-dimethyl-dodeca-2,6,8-trienoic acid (139944-50-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 74.6 percent / camphorsulfonic acid / toluene / 4.5 h / Ambient temperature

2: 93 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

3: 96.7 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C

4: 1.) DMSO, pyridine, CF₃COOH, 2.) dicyclohexylcarbodiimide / 1.) benzene, RT, 15 min, 2.) benzene, RT, 6 h

5: 1.) hexamethylphosphoric triamide (HMPA), potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, toluene, -78 deg C, 1 h

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; camphor-10-sulfonic acid; potassium hexamethylsilazane; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00034a036

upstream raw materials:

(S)-4-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyraldehyde

(R)-4-[(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-4-hydroxy-3-methyl-butyl)-2-methoxy-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

(S)-4-{(2R,4S,6R)-4-Hydroxy-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-hydroxy-1-methyl-propyl ester

(S)-4-{(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester

Downstream raw materials:

O-methyl-N-(4-methoxybenzyl)latrunculin A