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

Base Information

• Chemical Name: (R)-4-[(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6-(3-oxo-butyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one
• CAS No.: 139944-53-9
• Molecular Formula: C₂₇H₄₃NO₆SSi
• Molecular Weight: 537.793
• Mol file: 139944-53-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (R)-4-[(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6-(3-oxo-butyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-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:

(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) → (R)-4-[(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6-(3-oxo-butyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one (139944-53-9)

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.) lithium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, 0 deg C, 1 h, 2.) THF, 40 min

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; 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) → (R)-4-[(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6-(3-oxo-butyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one (139944-53-9)

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.) lithium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, 0 deg C, 1 h, 2.) THF, 40 min

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

DOI:10.1021/ja00034a036

Reference yield:

(R)-4-[3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one (101860-56-4,101977-01-9) → (R)-4-[(2R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6-(3-oxo-butyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one (139944-53-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 72.5 percent / 2 N aq. HCl / tetrahydrofuran / 24 h / Ambient temperature

2: 74.6 percent / camphorsulfonic acid / toluene / 4.5 h / Ambient temperature

3: 93 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 14 h / Ambient temperature

4: 96.7 percent / LiAlH₄ / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C

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

6: 1.) lithium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, 0 deg C, 1 h, 2.) THF, 40 min

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; camphor-10-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; 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