105228-46-4 Usage
Description
Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is an organic compound with a complex molecular structure, characterized by its chiral centers and functional groups. It is a versatile building block in the synthesis of various pharmaceutical compounds due to its unique properties and reactivity.
Uses
Used in Pharmaceutical Industry:
Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a key intermediate for the synthesis of various pharmaceutical compounds, including antimalarial, antitubercular, and antibiotic agents.
1. Antimalarial Applications:
Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a starting material for the synthesis of α-Amino-β-silyloxy-ester, which is a key intermediate in the preparation of the antimalarial drug quinine and its analogs. These compounds are essential in the treatment of malaria, a disease that affects millions of people worldwide.
2. Antitubercular Applications:
The compound is also used as a starting material for the synthesis of R,R-Formylglycine dimethylacetal, a key intermediate in the preparation of the tuberculostatic compound capreomycin IB. Capreomycin IB is an important drug used in the treatment of tuberculosis, particularly in cases where other antitubercular drugs are ineffective.
3. Antibiotic Applications:
Furthermore, Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used in the synthesis of 2R,5R,6S-2-(Methoxycarbonylmethyl)-5,6-diphenylmorpholine hydrochloride, a key intermediate for the preparation of the antibiotic (+)-negamycin. This antibiotic is effective against a range of bacterial infections and plays a crucial role in the treatment of various diseases.
Check Digit Verification of cas no
The CAS Registry Mumber 105228-46-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,5,2,2 and 8 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 105228-46:
(8*1)+(7*0)+(6*5)+(5*2)+(4*2)+(3*8)+(2*4)+(1*6)=94
94 % 10 = 4
So 105228-46-4 is a valid CAS Registry Number.
InChI:InChI=1/C24H21NO4/c26-21-16-25(24(27)28-17-18-10-4-1-5-11-18)22(19-12-6-2-7-13-19)23(29-21)20-14-8-3-9-15-20/h1-15,22-23H,16-17H2/t22-,23+/m1/s1
105228-46-4Relevant 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
Practical Asymmetric Syntheses of α-Amino Acids through Carbon-Carbon Bond Constructions on Electrophilic Glycine Templates
Williams, Robert M.,Sinclair, Peter J.,Zhai, Dongguan,Chen, Daimo
, p. 1547 - 1557 (2007/10/02)
The optically active D- and L-erythro-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) and D- and L-erythro-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) can be efficiently brominated to serve as electrophilic glycine templates for the asymmetric synthesis of amino acids.It was found that coupling to these templates can proceed with either net retention or net inversion of stereochemistry.The final deblocking to the amino acids is accomplished with either dissolving-metal reduction or catalytic hydrogenolysis.The syntheses of β-ethyl aspartic acid, norvaline, allylglycine, alanine, norleucine, homophenylalanine, p-methoxyhomophenylalanine, cyclopentylglycine, and cyclopentenylglycine and a formal synthesis of clavalanine are described.In addition, the direct asymmetric syntheses of N-t-BOC-allylglycine and N-t-BOC-cyclopentenylglycine are described.
