(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

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-butyric acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester
• CAS No.: 140146-99-2
• Molecular Formula: C₃₈H₆₇NO₈SSi₂
• Molecular Weight: 754.189
• Mol file: 140146-99-2.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-butyric acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester

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-butyric acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-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-(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

There total 3 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-butyric acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-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: 93.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (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) → (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)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 14h; Ambient temperature;

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-butyric acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester (140146-99-2)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; hydrogenchloride; dmap; camphor-10-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

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) → (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)

Guidance literature:

Multi-step reaction with 2 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

With 1H-imidazole; dmap; camphor-10-sulfonic acid; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00034a036

upstream raw materials:

tert-butyldimethylsilyl chloride

(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

(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

Downstream 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-butyraldehyde

(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

(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