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

Base Information

• Chemical Name: (4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde
• CAS No.: 145484-22-6
• Molecular Formula: C₂₁H₃₅NO₃Si
• Molecular Weight: 377.599
• Mol file: 145484-22-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde 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:

[(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-methanol (145452-01-3) → (4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde (145484-22-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 1.5h; Yield given;

DOI:10.1021/ja00052a096

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde (145484-22-6)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 25 h / 23 °C

2: p-TsOH*H₂O / benzene / 0.5 h / 80 °C

3: LiBH₄ / tetrahydrofuran; methanol / 20 h / 23 °C

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

With 1H-imidazole; lithium borohydride; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja973444c

Reference yield:

(2R,4R)-3-Benzyl-2-tert-butyl-4-((S)-1-hydroxy-2-methyl-propyl)-oxazolidine-4-carboxylic acid methyl ester (145451-90-7) → (4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde (145484-22-6)

Guidance literature:

Multi-step reaction with 5 steps

1: trifluoromethanesulfonic acid / methanol; H₂O / 6.5 h / 80 - 85 °C

2: imidazole / dimethylformamide / 25 h / 23 °C

3: p-TsOH*H₂O / benzene / 0.5 h / 80 °C

4: LiBH₄ / tetrahydrofuran; methanol / 20 h / 23 °C

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

With 1H-imidazole; lithium borohydride; oxalyl dichloride; trifluorormethanesulfonic acid; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja973444c

upstream raw materials:

[(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-methanol

tert-butyldimethylsilyl chloride

(2R,4R)-3-Benzyl-2-tert-butyl-4-((S)-1-hydroxy-2-methyl-propyl)-oxazolidine-4-carboxylic acid methyl ester

(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carboxylic acid methyl ester

Downstream raw materials:

(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

(1S,6R,7S,7aS)-6-Benzyl-7-hydroxy-7a-hydroxymethyl-1-isopropyl-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