tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

Base Information

• Chemical Name: tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• CAS No.: 112741-49-8
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.418
• Hs Code.: 2934999090
• European Community (EC) Number: 627-288-6
• DSSTox Substance ID: DTXSID90359675
• Nikkaji Number: J722.131B
• Wikidata: Q72503912
• Mol file: 112741-49-8.mol

Synonyms:112741-49-8;tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;(2R,3S)-TERT-BUTYL 6-OXO-2,3-DIPHENYLMORPHOLINE-4-CARBOXYLATE;tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate;(2R,3S)-(-)-N-Boc-6-oxo-2,3-diphenylmorpholine;MFCD00074955;173397-90-5;Tert-butyl-(2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;(2R,3S)-N-BOC-6-OXO-2,3- DIPHENYLMORPHOLINE;4-Morpholinecarboxylicacid, 6-oxo-2,3-diphenyl-, 1,1-dimethylethyl ester, (2R,3S)-;tert-Butyl(2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;SCHEMBL3706217;DTXSID90359675;MRUKRSQUUNYOFK-RBUKOAKNSA-N;(2R,3S)-tert-Butyl 6-oxo-2,3- diphenylmorpholine-4-carboxylate;STR08272;tert-butyl (2R,3S)-6-oxo-2,3-diphenyl-morpholine-4-carboxylate;SC3521;AKOS015918372;AC-3542;CS-W002317;AM802940;EN300-99393;J-002829;tert-Butyl(2>R,3S)-(-)-6-oxo-2,3-diphenyl-4-morph;(2R,3S)-(-)-N-Boc-6-oxo-2,3-diphenylmorpholine, 98%;(2R,3S)-(-)-2,3-Diphenyl-6-oxomorpholine, N-BOC protected;(5S,6R)-5,6-diphenyl-4-tert-butoxycarbonyl-morpholin-2-one;tert-butyl (5s,6r)-2-oxo-5,6-diphenylmorpholine-4-carboxylate;t-butyl (2R, 3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;t-butyl (2r,3s)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester;(2R,3S)-TERT-BUTYL6-OXO-2,3-DIPHENYLMORPHOLINE-4-CARBOXYLATE;tert-butyl (2R, 3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;tert-butyl- (2R, 3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate;(5S,6R)-4-(tert-butyoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine-2-one;(2R,3S)-tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate

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

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
• Solubility.: Acetone (Slightly, Heated, Sonicated), Chloroform (Slightly), DMSO (Slightly, So
• 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

(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylicAcidtert-ButylEster ^*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: Tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is a reactant used in the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G and colla gen cross-link pyridinolines. (2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester is a reactant used in the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G and collagen cross-link pyridinolines.

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

There total 9 articles about tert-Butyl (2R,3S)-(-)-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: 85.0%

(1'S,2'R)-ethyl N-(tert-butyloxycarbonyl)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate (112741-70-5) → tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate (112741-49-8,173397-90-5)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 120 ℃;

Reference yield: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester (100678-82-8) → tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate (112741-49-8,173397-90-5)

Guidance literature:

di-tert-butyl dicarbonate; 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester; In toluene; at 110 ℃; for 13h;

With toluene-4-sulfonic acid; In toluene; at 110 ℃; for 1h;

DOI:10.1039/c3cc45231j

Reference yield:

(1R,2S)-2-Amino-1,2-diphenylethanol (23190-16-1) → tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate (112741-49-8,173397-90-5)

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:

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

di-tert-butyl dicarbonate

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

2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester

Downstream raw materials:

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

(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-methyl-2'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(1'-prop-2'-enyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

(3S,5S,6R)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1'-pentynyl)-2,3,5,6-tetrahydro-1,4-oxazin-2-one

Refernces

• 1、 Yeo, David J.,Warriner, Stuart L.,Wilson, Andrew J.. "Monosubstituted alkenyl amino acids for peptide "stapling"". . p. 9131 - 9133. Retrieved 2013/09/24.
• 2、 Williams, Robert M.,Sinclair, Peter J.,DeMong, Duane E.,Chen, Daimo,Zhai, Dongguan. "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)-)]". . p. 18 - 30. Retrieved 2017/09/19.