(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester
• CAS No.: 116733-43-8
• Molecular Formula: C₁₂H₁₅NO₅
• Molecular Weight: 253.255
• Mol file: 116733-43-8.mol

Synonyms:(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester

Chemical Property of (1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester

There total 1 articles about (1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl 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:

3-[(E)-3-(methoxycarbonyl)-propenoyl]-oxazolidin-2-one (116733-42-7) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → (1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester (141435-12-3) + (1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester (116733-43-8)

Guidance literature:

With MS 4A; chiral tytanium reagent; In various solvent(s); Product distribution; other solvents;

DOI:10.1021/ja00196a045

Reference yield: 98.0%

(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester (116733-43-8) → (1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester (253454-00-1)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 19h;

DOI:10.1021/ol025600c

Reference yield: 85.0%

(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester (116733-43-8) → (1R,2R)-cyclohex-4-ene 1,2-dicarboxylic acid monomethyl ester (323196-38-9)

Guidance literature:

With lithium hydroxide; water; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1016/S0040-4039(00)01576-8

upstream raw materials:

3-[(E)-3-(methoxycarbonyl)-propenoyl]-oxazolidin-2-one

buta-1,3-diene

Downstream raw materials:

(1R,2R)-cyclohex-4-ene 1,2-dicarboxylic acid monomethyl ester

(1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester

(1R,2R)-2-aminocyclohexanecarboxylic acid methyl ester

(1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester

Refernces

• 1、 Narasaka, Koichi,Iwasawa, Nobuharu,Inoue, Masayuki,Yamada, Tohru,Nakashima, Masako,Sugimori, Jun. "Asymmetric Diels-Alder Reaction Catalyzed by a Chiral Titanium Reagent". . p. 5340 - 5345. Retrieved 2007/10/02.