(2S,3R)-Tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate

Base Information

• Chemical Name: (2S,3R)-Tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate
• CAS No.: 112741-50-1
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.418
• European Community (EC) Number: 627-150-5
• DSSTox Substance ID: DTXSID30359674
• Nikkaji Number: J1.603.936E
• Wikidata: Q72503914
• Mol file: 112741-50-1.mol

Synonyms:112741-50-1;tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;(2S,3R)-Tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate;tert-butyl (2S,3R)-6-oxo-2,3-diphenylmorpholine-4-carboxylate;(2S,3R)-N-BOC-6-OXO-2,3-DIPHENYLMORPHOLINE;(2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylmorpholine;Tert-Butyl-(2S,3R)-(+)-6-oxo-2,3-diphenyl-4- morpholinecarboxylate;(2S,3R)-(+)-N-tert-Butoxycarbonyl-6-oxo-2,3-diphenylmorpholine;N-Boc-(2S,3R)-(+)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylate;MFCD00074953;173397-90-5;N-Boc(2S, 3R)-(+)-6-oxo-2,3-diphenyl-4-morpholine carboxylate;SCHEMBL894292;2S,3R-6-OXO-2,3-DIPHENYL-4-MORPHOLINECARBOXYLATE;DTXSID30359674;(2S,3R)-tert-Butyl 6-oxo-2,3- diphenylmorpholine-4-carboxylate;tert-butyl (2S,3R)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;SC3531;tert-Butyl(2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;AKOS016842271;AC-1768;CS-W020639;DS-10716;W18730;(5R,6S)-(-)-4-Boc-5,6-diphenyl-2-morpholinone;(2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylmorpholine, 99%;(2S,3R)-Tert-butyl6-oxo-2,3-diphenylmorpholine-4-carboxylate;t-butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholine carboxylate;t-butyl (2s,3r)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;2-Oxo-5alpha,6alpha-diphenylmorpholine-4-carboxylic acid tert-butyl ester;(2S,3R)-tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate;(2S,3R)-N-Boc-6-oxo-2,3-diphenylmorpholine

Chemical Property of (2S,3R)-Tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.67E-10mmHg at 25°C
• Melting Point: 206 °C (dec.)(lit.)
• Refractive Index: 1.561
• Boiling Point: 509.6 °C at 760 mmHg
• PKA: -3.28±0.60(Predicted)
• Flash Point: 262 °C
• PSA: 55.84000
• Density: 1.175 g/cm³
• LogP: 4.20080
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 353.16270821
• Heavy Atom Count: 26
• Complexity: 501

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylmorpholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(=O)OC(C1C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC(=O)O[C@H]([C@H]1C2=CC=CC=C2)C3=CC=CC=C3
• Uses: (2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylmorpholine (Williams chiral auxiliary) can be used as a reactant: In the asymmetric synthesis of cylindrospermopsin and related alkaloids via an intramolecular 1,3-dipolar cycloaddition reaction.To synthesize boc-3-(1-methylcyclopropyl)-D-alanine, which is used as an intermediate to prepare 4-fluoroproline-based analogs as potent tripeptide thrombin inhibitors. In the total synthesis of potent hepatotoxic alkaloid 7-epicylindrospermopsin by intramolecular 1,3-dipolar cycloaddition and nitroaldol reaction.To prepare differentially functionalized diaminoglutamic acids via radical reaction of selenide with methyl 2-acetamidoacrylate.

Technology Process of (2S,3R)-Tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate

There total 5 articles about (2S,3R)-Tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate 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:

ethyl (1'R,2'S)-N-tert-butyloxycarbonyl-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate (112741-73-8) → (2S,3R)-tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate (112741-50-1,173397-90-5)

Guidance literature:

With toluene-4-sulfonic acid; calcium chloride; In benzene; for 8h; Heating;

DOI:10.1021/ja00213a031

Reference yield:

ethyl (1'R,2'S)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate (112835-62-8) → (2S,3R)-tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate (112741-50-1,173397-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / benzene / Heating

With toluene-4-sulfonic acid; In benzene;

DOI:10.1021/jo050603z

Reference yield:

(1S,2R)-2-Amino-1,2-diphenylethanol (23364-44-5) → (2S,3R)-tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate (112741-50-1,173397-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / tetrahydrofuran / 1 h / 20 °C

2: toluene / 10 h / Heating

3: p-TsOH*H₂O / toluene

With toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1055/s-2005-863740

upstream raw materials:

ethyl (1'R,2'S)-N-tert-butyloxycarbonyl-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate

di-tert-butyl dicarbonate

ethyl (1'R,2'S)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate

(1S,2R)-2-Amino-1,2-diphenylethanol

Downstream raw materials:

(3R,5R,6S)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1-prop-2-enyl)morpholin-2-one

(3R,5R,6S)-4-aza-5,6-diphenyl-2-oxo-1-oxabicyclo<4.3.0>nonane

(3S,3'S,4'R,6'S,8'R,8'aR)-1,2,3',4',8',8a'-hexahydro-6'-(2-methoxy-2-methylpropyl)-1',2-dioxo-3',4'-diphenylspiro[3H-indole-3,7'(6'H)-[1H]pyrrolo[2,1-c][1,4]oxazine]-8'-carboxylic acid ethyl ester

(5R,6S)-4-Oxy-5,6-diphenyl-5,6-dihydro-[1,4]oxazin-2-one

Refernces

• 1、 Ueda, Masafumi,Miyabe, Hideto,Teramachi, Masako,Miyata, Okiko,Naito, Takeaki. "Diastereoselective intermolecular radical addition to nitrones". . p. 6653 - 6660. Retrieved 2007/10/03.
• 2、 Williams, Robert M.,Sinclair, Peter J.,Zhai, Dongguan,Chen, Daimo. "Practical Asymmetric Syntheses of α-Amino Acids through Carbon-Carbon Bond Constructions on Electrophilic Glycine Templates". . p. 1547 - 1557. Retrieved 2007/10/02.