(2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl ester

Base Information

• Chemical Name: (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl ester
• CAS No.: 103959-51-9
• Molecular Formula: C₂₄H₃₉NO₄SSi
• Molecular Weight: 465.729
• Mol file: 103959-51-9.mol

Synonyms:

Chemical Property of (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl ester

There total 1 articles about (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl 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:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) + 2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline (102614-13-1) → (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl ester (103959-51-9)

Guidance literature:

With lithium diethylamide; Multistep reaction; 1) THF, -78 deg C, 2) -78 deg C;

DOI:10.1016/S0040-4039(00)79046-0

Reference yield:

(2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl ester (103959-51-9) → (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-phenyl-oxazol-4-yl)-hex-5-enal

Guidance literature:

Multi-step reaction with 5 steps

1: 1) Et₃N, 2) DIBAL / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 deg C

2: 65 percent / TiCl₄, Zn / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

3: 95 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / Heating

4: 90 percent / HF, pyridine

5: 98 percent / Dess-Martin oxidation

With pyridine; hydrogen fluoride; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)79046-0

Reference yield:

(2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanethioic acid S-tert-butyl ester (103959-51-9) → (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-phenyl-oxazol-4-yl)-hex-5-en-1-ol

Guidance literature:

Multi-step reaction with 4 steps

1: 1) Et₃N, 2) DIBAL / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 deg C

2: 65 percent / TiCl₄, Zn / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

3: 95 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / Heating

4: 90 percent / HF, pyridine

With pyridine; hydrogen fluoride; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)79046-0

upstream raw materials:

3-(tert-butyldimethylsilanyloxy)propionaldehyde

2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline

Downstream raw materials:

(2S,3S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-pentanal

4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-oxazole

(S)-4-[(1S,2S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-1-vinyl-butyl]-2-phenyl-4,5-dihydro-oxazole

C₂₇H₄₅NO₅Si₂