(4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone

Base Information

• Chemical Name: (4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone
• CAS No.: 917613-43-5
• Molecular Formula: C₂₃H₃₇NO₄Si
• Molecular Weight: 419.637
• Mol file: 917613-43-5.mol

Synonyms:(4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone

Chemical Property of (4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone

There total 4 articles about (4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone 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: 88.0%

(4R,2'R)-4-benzyl-3-(2'-hydroxyheptanoyl)-2-oxazolidinone (917613-31-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone (917613-43-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;

DOI:10.1021/ol0623365

Reference yield:

(R)-4-benzyl-3-heptanoyl-2-oxazolidinone (365569-51-3) → (4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone (917613-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / NaHMDS; Davis reagent / tetrahydrofuran / 1 h / -78 °C

2: 88 percent / imidazole / dimethylformamide / 2 h / 0 - 20 °C

With 1H-imidazole; Davis reagent; sodium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ol0623365

Reference yield:

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (4R,2'R)-4-benzyl-3-[2'-(t-butyldimethylsilyloxy)heptanoyl]-2-oxazolidinone (917613-43-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2: 94 percent / NaHMDS; Davis reagent / tetrahydrofuran / 1 h / -78 °C

3: 88 percent / imidazole / dimethylformamide / 2 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; Davis reagent; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ol0623365

upstream raw materials:

(4R,2'R)-4-benzyl-3-(2'-hydroxyheptanoyl)-2-oxazolidinone

tert-butyldimethylsilyl chloride

(R)-4-benzyl-3-heptanoyl-2-oxazolidinone

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

Downstream raw materials:

(R)-2-(t-butyldimethylsilyloxy)heptanoic acid benzyl ester

benzyl (R)‐2‐hydroxyheptanoate

N-Boc-N-Me-L-Ala-(R)-Hep(OBn)

benzyl (R)‐2‐(((6S,9R,12S)‐2,2,5,6,11,12‐hexamethyl‐4,7,10‐trioxo‐9‐pentyl‐3,8‐dioxa‐5,11‐diazatridecan‐13‐oyl)oxy)heptanoate