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

Base Information

• Chemical Name: (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one
• CAS No.: 250346-38-4
• Molecular Formula: C₂₉H₄₁NO₆Si
• Molecular Weight: 527.733
• Mol file: 250346-38-4.mol

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

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

There total 6 articles about (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)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: 60.0%

(3R)-3-(tert-butyldimethylsilyloxy)butanal (71171-66-9,92775-37-6,116839-04-4,72150-39-1) + (4R)-3-[2-(Phenylmethoxy)acetyl]-4-(phenylmethyl)oxazolidin-2-one (137238-71-2) → (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'S,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one + (4R,2'S,3'S,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one

Guidance literature:

(4R)-3-[2-(Phenylmethoxy)acetyl]-4-(phenylmethyl)oxazolidin-2-one; With tin(II) trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 ℃; for 1h;

(3R)-3-(tert-butyldimethylsilyloxy)butanal; With N,N,N,N,-tetramethylethylenediamine; In dichloromethane; at -78 ℃; for 2h; Further stages.;

DOI:10.1039/a909243i

Reference yield:

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one (250346-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / n-butyllithium / -78 °C

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

2.2: TMEDA / CH₂Cl₂ / cooling

With tin(II) trifluoromethanesulfonate; n-butyllithium; triethylamine; In dichloromethane;

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)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4-(phenylmethyl)oxazolidin-2-one (250346-38-4)

Guidance literature:

Multi-step reaction with 3 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

With tin(II) trifluoromethanesulfonate; n-butyllithium; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Cyclization / 2.1: Metallation / 2.2: Acylation / 3.1: Metallation / 3.2: Aldol reaction;

DOI:10.1039/a909243i

upstream raw materials:

(3R)-3-(tert-butyldimethylsilyloxy)butanal

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

(R)-4-(phenylmethyl)-2-oxazolidinone

(R)-2-amino-3-phenylpropanol

Downstream raw materials:

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

C₃₂H₄₀O₈Si

(2S,3R,5R)-5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexanal

(2S,3R,5R)-5-(tert-Butyldimethylsilyloxy)-2-(phenylmethoxy)-3-(triethylsilyloxy)hexan-1-ol