(2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester

Base Information

• Chemical Name: (2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester
• CAS No.: 203934-88-7
• Molecular Formula: C₂₅H₄₃NO₅Si
• Molecular Weight: 465.706
• Mol file: 203934-88-7.mol

Synonyms:

Chemical Property of (2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester

There total 1 articles about (2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl 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:

[1-methoxyprop-1-enyloxy]trimethylsilane (34880-70-1) + (4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde (145484-22-6) → (2S,3R)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester + (2S,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester + (2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester (203934-88-7)

Guidance literature:

With potassium carbonate; magnesium iodide; Mechanism; multistep reaction, other trimethylsilyl enol ethers;

DOI:10.1021/ja973444c

Reference yield:

(2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester (203934-88-7) → Lactacystin (133343-34-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) i-Pr₂NEt, H₂ / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h

2: 48percent HF / acetonitrile / 24 h / 23 °C

3: Et₃N, oxalyl chloride, DMSO / CH₂Cl₂ / 2 h / -78 °C

4: 1.) NaClO₂, 20percent aq. NaH₂PO₄, 2.) 1,3-propanedithiol, HCl / 1.) t-BuOH, 2-methyl-2-butene, 23 deg C, 1 h, 2.) CF₃CH₂OH, 50-55 deg C, 7.5 h

5: 93 percent / Et₃N, bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 0.5 h / 23 °C

6: 880.0 mg / Et₃N / CH₂Cl₂ / 4 h / 23 °C

With 1.3-propanedithiol; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; hydrogen fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; acetonitrile;

DOI:10.1021/ja973444c

Reference yield:

(2R,3S)-3-[(4S,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-3-hydroxy-2-methyl-propionic acid methyl ester (203934-88-7) → omuralide (154226-60-5,186833-31-8,155975-72-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) i-Pr₂NEt, H₂ / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h

2: 48percent HF / acetonitrile / 24 h / 23 °C

3: Et₃N, oxalyl chloride, DMSO / CH₂Cl₂ / 2 h / -78 °C

4: 1.) NaClO₂, 20percent aq. NaH₂PO₄, 2.) 1,3-propanedithiol, HCl / 1.) t-BuOH, 2-methyl-2-butene, 23 deg C, 1 h, 2.) CF₃CH₂OH, 50-55 deg C, 7.5 h

5: 93 percent / Et₃N, bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 0.5 h / 23 °C

With 1.3-propanedithiol; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; hydrogen fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; acetonitrile;

DOI:10.1021/ja973444c

upstream raw materials:

[1-methoxyprop-1-enyloxy]trimethylsilane

(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde

Downstream raw materials:

(1S,6R,7S,7aS)-7a-(tert-Butyl-dimethyl-silanyloxymethyl)-7-hydroxy-1-isopropyl-6-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

(1S,6R,7S,7aS)-7-Hydroxy-1-isopropyl-6-methyl-5-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbaldehyde

(1S,6R,7S,7aS)-7-Hydroxy-7a-hydroxymethyl-1-isopropyl-6-methyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

(3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid