(2R,3S)-1-Chloro-3-(dibenzylamino)-5-methylhexan-2-ol

Base Information

• Chemical Name: (2R,3S)-1-Chloro-3-(dibenzylamino)-5-methylhexan-2-ol
• CAS No.: 171815-92-2
• Molecular Formula: C21H28 Cl N O
• Molecular Weight: 345.91
• DSSTox Substance ID: DTXSID20444189
• Wikidata: Q82262244
• Mol file: 171815-92-2.mol

Synonyms:171815-92-2;(2R,3S)-1-Chloro-3-(dibenzylamino)-5-methylhexan-2-ol;(2R,3S)-1-Chloro-3-dibenzylamino-5-methylhexan-2-ol;DTXSID20444189;VPTZKLYFCBJELX-SFTDATJTSA-N;2-Hexanol,3-[bis(phenylmethyl)amino]-1-chloro-5-methyl-,[r-(r*,s*)]-(9ci)

Chemical Property of (2R,3S)-1-Chloro-3-(dibenzylamino)-5-methylhexan-2-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 453.8°Cat760mmHg
• PKA: 13.54±0.20(Predicted)
• Flash Point: 228.3°C
• PSA: 23.47000
• Density: 1.095g/cm³
• LogP: 4.70320
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 345.1859422
• Heavy Atom Count: 24
• Complexity: 304

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-1-CHLORO-3-DIBENZYLAMINO-5-METHYLHEXAN-2-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2R,3S)-1-Chloro-3-(dibenzylamino)-5-methylhexan-2-ol

There total 5 articles about (2R,3S)-1-Chloro-3-(dibenzylamino)-5-methylhexan-2-ol 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: 82.0%

(S)-1-Chloro-3-dibenzylamino-5-methyl-hexan-2-one (171815-95-5) → (2R,3S)-3-(Dibenzylamino)-1-chloro-5-methylhexan-2-ol (171815-92-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -100 ℃; for 6h;

DOI:10.1021/jo00126a019

Reference yield: 82.0%

(2R,1'S)-2-[1-(dibenzylamino)-3-methylbutyl]oxirane (171815-93-3) → (2R,3S)-3-(Dibenzylamino)-1-chloro-5-methylhexan-2-ol (171815-92-2)

Guidance literature:

With chloro-trimethyl-silane; acetic acid; In acetonitrile; for 6h; Heating;

DOI:10.1021/jo0514873

Reference yield:

L-Leucine ethyl ester (2743-60-4,75023-21-1) → (2R,3S)-3-(Dibenzylamino)-1-chloro-5-methylhexan-2-ol (171815-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1: (i-Pr)2NEt / CHCl₃ / 5 h / Heating

2: 90 percent / LiBr, MeLi / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

3: 82 percent / LiAlH₄ / tetrahydrofuran / 6 h / -100 °C

With lithium aluminium tetrahydride; methyllithium; N-ethyl-N,N-diisopropylamine; lithium bromide; In tetrahydrofuran; diethyl ether; chloroform;

DOI:10.1021/jo00126a019

upstream raw materials:

(S)-1-Chloro-3-dibenzylamino-5-methyl-hexan-2-one

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

L-Leucine ethyl ester

benzyl bromide

Downstream raw materials:

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