(4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one

Base Information

• Chemical Name: (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one
• CAS No.: 250346-41-9
• Molecular Formula: C₃₅H₅₅NO₆Si₂
• Molecular Weight: 641.996
• Mol file: 250346-41-9.mol

Synonyms:(4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one

Chemical Property of (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one

There total 7 articles about (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one 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: 84.0%

triethylsilyl chloride (994-30-9) + (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one (250346-38-4) → (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one (250346-41-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1039/a909243i

Reference yield:

(4R)-3-[2-(Phenylmethoxy)acetyl]-4-(phenylmethyl)oxazolidin-2-one (137238-71-2) → (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one (250346-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tin(II) trifluoromethanesulfonate; triethylamine / CH₂Cl₂ / -78 °C

1.2: TMEDA / CH₂Cl₂ / cooling

2.1: 84 percent / imidazole / dimethylformamide

With 1H-imidazole; tin(II) trifluoromethanesulfonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol991020c

Reference yield:

(R)-2-amino-3-phenylpropanol (5267-64-1) → (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one (250346-41-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / K₂CO₃ / 6 h / 135 - 140 °C

2.1: n-BuLi / tetrahydrofuran / 1.5 h / -78 - -20 °C

2.2: 84 percent / tetrahydrofuran / 0.5 h / -78 °C

3.1: Sn(OTf)2; NEt₃ / CH₂Cl₂ / 1 h / -78 °C

3.2: 60 percent / TMEDA / CH₂Cl₂ / 2 h / -78 °C

4.1: 84 percent / imidazole / dimethylformamide / 0 - 20 °C

With 1H-imidazole; tin(II) trifluoromethanesulfonate; n-butyllithium; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Cyclization / 2.1: Metallation / 2.2: Acylation / 3.1: Metallation / 3.2: Aldol reaction / 4.1: Etherification;

DOI:10.1039/a909243i

upstream raw materials:

triethylsilyl chloride

(4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one

(4R)-3-[2-(Phenylmethoxy)acetyl]-4-(phenylmethyl)oxazolidin-2-one

(R)-2-amino-3-phenylpropanol

Downstream raw materials:

(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hex-1-yl acetate

(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate

(2'R,3'R,5'R)-2-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol