Acetic acid (2R,3S)-3-dibenzylamino-2-hydroxy-5-methylhexyl ester

Base Information

• Chemical Name: Acetic acid (2R,3S)-3-dibenzylamino-2-hydroxy-5-methylhexyl ester
• CAS No.: 871948-93-5
• Molecular Formula: C23H31 N O3
• Molecular Weight: 369.5
• DSSTox Substance ID: DTXSID701007397
• Nikkaji Number: J2.521.476E
• Wikidata: Q83003385
• Mol file: 871948-93-5.mol

Synonyms:871948-93-5;Acetic acid (2R,3S)-3-dibenzylamino-2-hydroxy-5-methylhexyl ester;DTXSID701007397;AKOS015911929;3-(dibenzylamino)-2-hydroxy-5-methylhexyl acetate;Acetic acid(2R,3S)-3-dibenzylamino-2-hydroxy-5-methylhexyl ester

Chemical Property of Acetic acid (2R,3S)-3-dibenzylamino-2-hydroxy-5-methylhexyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 503.731°C at 760 mmHg
• Flash Point: 258.447°C
• PSA: 49.77000
• Density: 1.084g/cm³
• LogP: 4.02750
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 369.23039385
• Heavy Atom Count: 27
• Complexity: 394

Purity/Quality:

97% ^*data from raw suppliers

ACETIC ACID (2R,3S)-3-DIBENZYLAMINO-2-HYDROXY-5-METHYLHEXYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Acetic acid (2R,3S)-3-dibenzylamino-2-hydroxy-5-methylhexyl ester

There total 4 articles about Acetic acid (2R,3S)-3-dibenzylamino-2-hydroxy-5-methylhexyl 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: 67.0%

(4R)-4-[(S)-1-(dibenzylamino)-3-methylbutyl]-1,3-dioxolan-2-one (952526-14-6) + methyllithium (917-54-4) → (2R,3S)-O1-acetyl-3-(dibenzylamino)-5-methylhexane-1,2-diol (871948-93-5)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo070829x

Reference yield: 63.0%

acetic acid (64-19-7,77671-22-8) + (2R,1'S)-2-[1-(dibenzylamino)-3-methylbutyl]oxirane (171815-93-3) → (2R,3S)-O1-acetyl-3-(dibenzylamino)-5-methylhexane-1,2-diol (871948-93-5)

Guidance literature:

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; In acetonitrile; at 80 ℃; for 12h;

DOI:10.1021/jo0514873

Reference yield:

(2R,1'S)-2-[1-(dibenzylamino)-3-methylbutyl]oxirane (171815-93-3) → (2R,3S)-O1-acetyl-3-(dibenzylamino)-5-methylhexane-1,2-diol (871948-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BF₃*OEt₂; diisopropylamine / diethyl ether / 0.33 h / 20 °C

1.2: 91 percent / diethyl ether; H₂O / 0.17 h / 20 °C

2.1: 67 percent / tetrahydrofuran / 0.5 h / -78 °C

With boron trifluoride diethyl etherate; diisopropylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo070829x

upstream raw materials:

acetic acid

(2R,1'S)-2-[1-(dibenzylamino)-3-methylbutyl]oxirane

(4R)-4-[(S)-1-(dibenzylamino)-3-methylbutyl]-1,3-dioxolan-2-one

methyllithium

Downstream raw materials:

(2R,3S)-3-(dibenzylamino)-5-methylhexane-1,2-diol