Carbamic acid, ((1S,2S,4R)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)-5-((phenylmethyl)amino)pentyl)-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, ((1S,2S,4R)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)-5-((phenylmethyl)amino)pentyl)-, 1,1-dimethylethyl ester
• CAS No.: 126409-25-4
• Molecular Formula: C31H38 N2 O4
• Molecular Weight: 502.654
• DSSTox Substance ID: DTXSID30155178
• Wikidata: Q83022939
• Mol file: 126409-25-4.mol

Synonyms:126409-25-4;N-t-Butyloxycarbonyl-5-amino-1,6-diphenyl-4-hydroxy-2-(N-benzylcarbamoyl)hexane;Carbamic acid, ((1S,2S,4R)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)-5-((phenylmethyl)amino)pentyl)-, 1,1-dimethylethyl ester;Carbamic acid, [(1S,2S,4R)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)-5-[(phenylmethyl)amino]pentyl]-, 1,1-dimethylethyl ester;Boc-CH2Ph-NHBn deriv.;DTXSID30155178;isopropyl N-[(1S,2S,4R)-1,4-dibenzyl-5-(benzylamino)-2-hydroxy-5-oxo-pentyl]carbamate

Chemical Property of Carbamic acid, ((1S,2S,4R)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)-5-((phenylmethyl)amino)pentyl)-, 1,1-dimethylethyl ester

Chemical Property:

• Vapor Pressure: 6.54E-22mmHg at 25°C
• Boiling Point: 722.5°Cat760mmHg
• Flash Point: 390.8°C
• Density: 1.147g/cm³
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 488.26750763
• Heavy Atom Count: 36
• Complexity: 637

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)NC(CC1=CC=CC=C1)C(CC(CC2=CC=CC=C2)C(=O)NCC3=CC=CC=C3)O
• Isomeric SMILES: CC(C)OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](C[C@@H](CC2=CC=CC=C2)C(=O)NCC3=CC=CC=C3)O

Technology Process of Carbamic acid, ((1S,2S,4R)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)-5-((phenylmethyl)amino)pentyl)-, 1,1-dimethylethyl ester

There total 38 articles about Carbamic acid, ((1S,2S,4R)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)-5-((phenylmethyl)amino)pentyl)-, 1,1-dimethylethyl ester 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: 74.0%

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one (98818-41-8) + benzylamine (100-46-9) → (2R,4S,5S)-N,2-dibenzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanamide (126409-25-4)

Guidance literature:

With trimethylaluminum; In dichloromethane; 1) 23 deg C, 10 min, 2) 40 deg C, 3 h;

DOI:10.1021/jo00023a009

Reference yield:

D-Mannose (530-26-7) → (2R,4S,5S)-N,2-dibenzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanamide (126409-25-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 3percent H₂SO₄ / 12 h / 23 °C

2: 1) CCl₄, (Me₂N)3P, 2) Li, NH₃ / 1a) THF, -78 deg C, 30 min, b) 23 deg C, 30 min, 2) -78 deg C to 0 deg C, 5 h

3: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 0 deg C to 23 deg C

4: H₂ / 10percent Pd-C / ethyl acetate; methanol / 5 h

5: 84 percent / 40percent aq. AcOH / 3 h / 90 °C

6: pyridine / 12 h / 0 deg C to 23 deg C

7: NaOMe / CHCl₃ / 1) 0 deg C, 10 min, 2) 23 deg C, 4 h

8: 91 percent / CuI / tetrahydrofuran / 3 h / -40 deg C to 0 deg C

9: 92 percent / Ph₃P, EtO₂CN=NCO₂Et, Ph₂P(O)N₃ / toluene / 12 h / -10 deg C to 23 deg C

10: 72 percent / m-chloroperbenzoic acid, BF₃*OEt₂ / CH₂Cl₂ / 3 h / 0 °C

11: 91 percent / H₂ / 10percent Pd-C / ethyl acetate / 6 h

12: 1) lithium tetramethyldisilazide / 1) THF, -78 deg C, 30 min, 2) -78 deg C, 30 min

13: 74 percent / Me₃Al / CH₂Cl₂ / 1) 23 deg C, 10 min, 2) 40 deg C, 3 h

With pyridine; tetrachloromethane; copper(l) iodide; lithium tetramethyldisilazide; sulfuric acid; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; ammonia; hydrogen; trimethylaluminum; sodium methylate; pyridinium p-toluenesulfonate; lithium; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; Hexamethylphosphorous triamide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; ethyl acetate; toluene;

DOI:10.1021/jo00023a009

Reference yield:

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabinohex-1-enitol (68144-11-6) → (2R,4S,5S)-N,2-dibenzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanamide (126409-25-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 0 deg C to 23 deg C

2: H₂ / 10percent Pd-C / ethyl acetate; methanol / 5 h

3: 84 percent / 40percent aq. AcOH / 3 h / 90 °C

4: pyridine / 12 h / 0 deg C to 23 deg C

5: NaOMe / CHCl₃ / 1) 0 deg C, 10 min, 2) 23 deg C, 4 h

6: 91 percent / CuI / tetrahydrofuran / 3 h / -40 deg C to 0 deg C

7: 92 percent / Ph₃P, EtO₂CN=NCO₂Et, Ph₂P(O)N₃ / toluene / 12 h / -10 deg C to 23 deg C

8: 72 percent / m-chloroperbenzoic acid, BF₃*OEt₂ / CH₂Cl₂ / 3 h / 0 °C

9: 91 percent / H₂ / 10percent Pd-C / ethyl acetate / 6 h

10: 1) lithium tetramethyldisilazide / 1) THF, -78 deg C, 30 min, 2) -78 deg C, 30 min

11: 74 percent / Me₃Al / CH₂Cl₂ / 1) 23 deg C, 10 min, 2) 40 deg C, 3 h

With pyridine; copper(l) iodide; lithium tetramethyldisilazide; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; hydrogen; trimethylaluminum; sodium methylate; pyridinium p-toluenesulfonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; ethyl acetate; toluene;

DOI:10.1021/jo00023a009

upstream raw materials:

lithium benzylamide

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

(4S,5S)-4-Benzyl-5-((R)-2-benzylcarbamoyl-3-phenyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

benzylamine

Refernces

• 1、 Ghosh,Fidanze. "Transition-state mimetics for HIV protease inhibitors: Stereocontrolled synthesis of hydroxyethylene and hydroxyethylamine isosteres by ester- derived titanium enolate syn and anti-aldol reactions". . p. 6146 - 6152. Retrieved 2007/10/03.
• 2、 Ghosh, Arun K.,McKee, Sean P.,Thompson, Wayne J.. "An Efficient Synthesis of Hydroxyethylene Dipeptide Isosteres: The Core Unit of Potent HIV-1 Protease Inhibitors". . p. 6500 - 6503. Retrieved 2007/10/02.