(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

Base Information

• Chemical Name: (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
• CAS No.: 139944-42-6
• Molecular Formula: C₂₅H₃₇NO₈S
• Molecular Weight: 511.637
• Mol file: 139944-42-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 72.5%

(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,4R,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 (140146-98-1) + (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)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/ja00034a036

Reference yield: 74.6%

methanol (67-56-1) + (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) → (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)

Guidance literature:

With camphor-10-sulfonic acid; In toluene; for 4.5h; Ambient temperature;

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) → latrunculin A (76343-93-6)

Guidance literature:

Multi-step reaction with 11 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.) tert-butyllithium, 2.) O₂ / 1.) THF, pentane, -78 deg C, 5 min

5: 76.8 percent / Al₂O₃, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 78.4 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

7: 1.) sodium bis(trimethylsilyl)amide, hexamethylphosphoric triamide (HMPA) / 1.) THF, -78 deg C, 30 min, 2.) THF, 30 min

8: 89.3 percent / pyridine*(HF)x / tetrahydrofuran / 1 h / 0 °C

9: 28 percent / PPh₃, diethyl azodicarboxylate (DEAD) / benzene / 48 h / Ambient temperature

10: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.05 h / Ambient temperature

11: 49 percent / 3 N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; aluminum oxide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; oxygen; sodium hexamethyldisilazane; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00034a036

upstream raw materials:

(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:

(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

latrunculin A

latrunculin B

(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