(2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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-Hydroxy-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.:139944-51-7
Molecular Formula:C₃₁H₄₃NO₇S
Molecular Weight:573.751
Hs Code.:

(2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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

Synonyms:(2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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

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Chemical Property of (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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

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Technology Process of (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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 7 articles about (2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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:

: 140146-97-0
(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

: 139944-51-7
(2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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

Guidance literature:: Multi-step reaction with 5 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

5: 96 percent / pyridine*(HF)x / tetrahydrofuran / 0 - 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; potassium hexamethylsilazane; pyridine hydrogenfluoride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja00034a036

Reference yield:

: 140146-99-2
(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

: 139944-51-7
(2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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

Guidance literature:: Multi-step reaction with 4 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

4: 96 percent / pyridine*(HF)x / tetrahydrofuran / 0 - 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; potassium hexamethylsilazane; pyridine hydrogenfluoride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja00034a036

Reference yield:

: 139944-42-6
(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

: 139944-51-7
(2Z,6E,8Z)-(S)-12-{(2R,4S,6R)-4-Hydroxy-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

Guidance literature:: Multi-step reaction with 6 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

6: 96 percent / pyridine*(HF)x / tetrahydrofuran / 0 - 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; camphor-10-sulfonic acid; potassium hexamethylsilazane; pyridine hydrogenfluoride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00034a036