Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

Base Information

• Chemical Name: Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• CAS No.: 105228-46-4
• Molecular Formula: C24H21NO4
• Molecular Weight: 387.435
• Hs Code.: 29349990
• European Community (EC) Number: 620-833-9
• DSSTox Substance ID: DTXSID50359676
• Nikkaji Number: J974.323E
• Wikidata: Q72441690
• Mol file: 105228-46-4.mol

Synonyms:105228-46-4;(2S,3R)-Benzyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate;Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;benzyl (2S,3R)-6-oxo-2,3-diphenylmorpholine-4-carboxylate;(2S,3R)-(+)-N-Z-6-oxo-2,3-diphenylmorpholine;(2S,3R)-N-CBZ-6-OXO-2,3- DIPHENYLMORPHOLINE;(2S,3R)-benzyl 6-oxo-2,3- diphenylmorpholine-4-carboxylate;Benzyl(2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;DTXSID50359676;CS-B0131;MFCD00074956;SC3381;AKOS016842864;AC-4320;4-Morpholinecarboxylic acid, 6-oxo-2,3-diphenyl-, phenylmethyl ester, (2S,3R)-;AS-54651;A801168;(2S,3R)-(+)-N-Z-6-oxo-2,3-diphenylmorpholine, 99%;(2S,3R)-Benzyl6-oxo-2,3-diphenylmorpholine-4-carboxylate;(5S,6R)-(+)-4-Benzyloxycarbonyl-5,6-diphenyl-2-morpholinone;4-Morpholinecarboxylic acid,6-oxo-2,3-diphenyl-,phenylMethyl ester,(2S,3R)-

Chemical Property of Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

Chemical Property:

• Vapor Pressure: 1.33E-13mmHg at 25°C
• Melting Point: 205-207 °C(lit.)
• Refractive Index: 1.609
• Boiling Point: 583.5 °C at 760 mmHg
• PKA: -3.33±0.60(Predicted)
• Flash Point: 306.7 °C
• PSA: 55.84000
• Density: 1.242 g/cm³
• LogP: 4.60250
• Storage Temp.: 2-8°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 387.14705815
• Heavy Atom Count: 29
• Complexity: 547

Purity/Quality:

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

(2S,3R)-Benzyl6-Oxo-2,3-diphenylmorpholine-4-carboxylate ^*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: C1C(=O)OC(C(N1C(=O)OCC2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1C(=O)O[C@H]([C@H](N1C(=O)OCC2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
• Uses: (2S,3R)-(+)-N-Z-6-oxo-2,3-diphenylmorpholine can be used as a starting material for the synthesis of:α-Amino-β-silyloxy-ester, a key intermediate for the preparation of antimalarial drug quinine and its analogs.R, R-Formylglycine dimethylacetal, a key intermediate for the preparation of tuberculostatic compound capreomycin IB.2R,5R,6S-2-(Methoxycarbonylmethyl)-5,6-diphenylmorpholine hydrochloride, a key intermediate for the preparation of an antibiotic (+)-negamycin.

Technology Process of Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

There total 7 articles about Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate 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-(1',2'-diphenyl-2'-hydroxyethyl)glycinate (112835-62-8) → (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (105228-46-4,335159-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

2: p-TsOH*H₂O / toluene

With sodium hydrogencarbonate; toluene-4-sulfonic acid; In dichloromethane; toluene;

DOI:10.1055/s-2005-863740

Reference yield:

(1S,2R)-2-Amino-1,2-diphenylethanol (23364-44-5) → (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (105228-46-4,335159-14-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: aq. NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

3: p-TsOH*H₂O / toluene

With sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1055/s-2005-863740

Reference yield:

erythro-2-amino-1,2-diphenylethanol (530-36-9,3764-63-4,13286-63-0,23190-16-1,23190-17-2,23364-44-5,23412-95-5,39664-87-4,88082-66-0) → (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (105228-46-4,335159-14-3)

Guidance literature:

Multi-step reaction with 4 steps

2: Et₃N / tetrahydrofuran / 25 °C

3: NaHCO₃ / CH₂Cl₂; H₂O

4: p-TsOH / benzene / Heating

With sodium hydrogencarbonate; triethylamine; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; benzene;

DOI:10.1021/ja00265a053

upstream raw materials:

[Benzyloxycarbonyl-((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-amino]-acetic acid ethyl ester

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

ethyl bromoacetate

benzyl chloroformate

Downstream raw materials:

(3R,5R,6S)-3-tert-Butoxycarbonylmethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

(5R,6S)-2-hydroxy-2-methyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

(2R,5R,6S)-2-(tert-butyldimethylsilyloxy)-2-ethoxycarbonylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

(3R,5R,6S)-3-Diethoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Refernces

• 1、 Schuerman, Marla A.,Keverline, Kathryn I.,Hiskey, Richard G.. "Chiral Synthesis of L-γ-Carboxylgutamic Acid (L-Gla)". . p. 825 - 828. Retrieved 2007/10/02.
• 2、 Sinclair, Peter J.,Zhai, Dongguan,Reibenspies, Joseph,Williams, Robert M.. "Electrophilic Glycinates: New and Versatile Templates for Asymmetric Amino Acid Synthesis". . p. 1103 - 1104. Retrieved 2007/10/02.