112741-50-1 Usage
Description
tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate, also known as (2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylmorpholine, is a chiral auxiliary derived from morpholine. It is characterized by its unique stereochemistry and structural features, which make it a valuable compound in the field of organic chemistry and pharmaceutical synthesis. Its Boc-protected structure ensures the stability of the molecule during various chemical reactions, while the phenyl groups provide steric hindrance and influence the reactivity of the molecule.
Uses
Used in Asymmetric Synthesis:
tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a chiral auxiliary for the asymmetric synthesis of complex organic molecules, such as cylindrospermopsin and related alkaloids. Its unique stereochemistry and structural features enable the selective formation of desired enantiomers, which is crucial in the development of pharmaceuticals and agrochemicals.
Used in Synthesis of Thrombin Inhibitors:
In the pharmaceutical industry, tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a reactant to synthesize boc-3-(1-methylcyclopropyl)-D-alanine, an intermediate in the preparation of 4-fluoroproline-based analogs. These analogs are potent tripeptide thrombin inhibitors, which have therapeutic applications in the treatment of various blood clot-related disorders.
Used in Total Synthesis of Hepatotoxic Alkaloids:
tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is employed in the total synthesis of potent hepatotoxic alkaloid 7-epicylindrospermopsin. tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is synthesized through a combination of intramolecular 1,3-dipolar cycloaddition and nitroaldol reactions, showcasing the versatility of the chiral auxiliary in complex organic synthesis.
Used in Preparation of Diversely Functionalized Diaminoglutamic Acids:
In the field of amino acid chemistry, tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used to prepare differentially functionalized diaminoglutamic acids. This is achieved through a radical reaction of selenide with methyl 2-acetamidoacrylate, which can lead to the development of novel bioactive compounds with potential applications in the pharmaceutical industry.
Check Digit Verification of cas no
The CAS Registry Mumber 112741-50-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,7,4 and 1 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 112741-50:
(8*1)+(7*1)+(6*2)+(5*7)+(4*4)+(3*1)+(2*5)+(1*0)=91
91 % 10 = 1
So 112741-50-1 is a valid CAS Registry Number.
InChI:InChI=1/C21H23NO4/c1-21(2,3)26-20(24)22-14-17(23)25-19(16-12-8-5-9-13-16)18(22)15-10-6-4-7-11-15/h4-13,18-19H,14H2,1-3H3
112741-50-1Relevant articles and documents
An improved synthesis of optically pure 4-Boc-5,6-diphenylmorpholin-2-one and 4-Cbz-5,6-diphenylmorpholin-2-one
Dastlik, Kim A.,Sundermeier, Uta,Johns, Deidre M.,Chen, Yuyin,Williams, Robert M.
, p. 693 - 696 (2007/10/03)
A convenient synthesis of optically pure 4-Boc-5,6-diphenylmorpholin-2-one and 4-Cbz-5,6-diphenylmorpholin-2-one by reaction of (+)- or (-)-2-amino-1,2-diphenylethanol with ethyl bromoacetate, followed by N-protection, and p-TsOH-mediated ring-closure is
Asymmetric synthesis of N-tert-butoxycarbonyl α- Amino acids. synthesis of (5S,6R)-4-tert-butoxycarbonyl-5,6-diphenylmorpholin-2-ONE [(4-Morpholinecarboxylic acid, 6-oxo-2,3-diphenyl-, 1,1-dimethylethyl ester, (2S,3R)-)]
Williams, Robert M.,Sinclair, Peter J.,DeMong, Duane E.,Chen, Daimo,Zhai, Dongguan
, p. 18 - 30 (2017/09/19)
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