(2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 209003-87-2
• Molecular Formula: C₁₉H₂₅NO₄
• Molecular Weight: 331.412
• Mol file: 209003-87-2.mol

Synonyms:(2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

There total 2 articles about (2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl 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:

4-but-1-enylmagnesium bromide (7103-09-5) + Weinreb amide (164530-43-2) → (2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester (209003-87-2)

Guidance literature:

In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(98)00508-0

Reference yield:

(2R,4R)-2-carboxy-4-phenyl-3-tert-butoxycarbonyloxazolidine (164530-42-1) → (2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester (209003-87-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) triethylamine / 1.) THF, -20 deg C, 0.5 h, 2.) THF, DMF, 0 deg C, 2 h

2: 6.3 g / diethyl ether / 0.5 h / 0 °C

With 4-methyl-morpholine; triethylamine; isobutyl chloroformate; In diethyl ether;

DOI:10.1016/S0040-4020(98)00508-0

Reference yield:

(2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester (209003-87-2) → (2S,3R,6S)-3-benzyloxy-6-dodecyl-2-vinylpiperidine (209003-96-3)

Guidance literature:

Multi-step reaction with 10 steps

1: NaBH₄ / ethanol / -78 °C

2: 98 percent / NaH, N(Bu₄)I / tetrahydrofuran / Ambient temperature

3: 78 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O / Ambient temperature

4: diethyl ether / Ambient temperature

5: PDC / CH₂Cl₂ / Ambient temperature

6: 1.) CF₃COOH / 1.) ClCH₂CH₂Cl, rt.; 2.) water

7: 1.) AgBF₄; 2.) Zn(BH₄)2 / 1.) THF, -78 deg C

8: 86 percent / tetrahydrofuran / Ambient temperature

9: thionyl chloride / tetrahydrofuran / Ambient temperature

10: KCN / dimethylsulfoxide; tetrahydrofuran

With potassium cyanide; sodium tetrahydroborate; sodium periodate; dipyridinium dichromate; silver tetrafluoroborate; thionyl chloride; zinc(II) tetrahydroborate; tetra-(n-butyl)ammonium iodide; sodium hydride; trifluoroacetic acid; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)00646-7

upstream raw materials:

4-but-1-enylmagnesium bromide

Weinreb amide

(2R,4R)-2-carboxy-4-phenyl-3-tert-butoxycarbonyloxazolidine

Downstream raw materials:

(2R,4R,1'S)-2-(1'-hydroxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

(2R,4R,1'R)-2-(1'-hydroxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

(2S,3R,6S)-3-benzyloxy-6-dodecyl-2-vinylpiperidine

(3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine