(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

Base Information

• Chemical Name: (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
• CAS No.: 139944-35-7
• Molecular Formula: C₂₈H₄₅NO₆SSi
• Molecular Weight: 551.82
• Mol file: 139944-35-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 6 articles about (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 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: 6.2%

(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 (140146-99-2) → (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 (139944-43-7) + (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 (139944-35-7)

Guidance literature:

With diisobutylaluminium hydride; In hexane; at -78 ℃; for 0.5h;

DOI:10.1021/ja00034a036

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) → (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 (139944-35-7)

Guidance literature:

Multi-step reaction with 3 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

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

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) → (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 (139944-35-7)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/ja00034a036

upstream raw materials:

(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-(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

(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

(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

Downstream raw materials:

(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

(2Z,6Z)-(S)-10-{(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}-3,8-dimethyl-deca-2,6-dienoic acid

(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

latrunculin B