1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-

Base Information

• Chemical Name: 1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-
• CAS No.: 200616-22-4
• Molecular Formula: C24H27NO2
• Molecular Weight: 361.484
• DSSTox Substance ID: DTXSID60464583
• Wikidata: Q82289966
• Mol file: 200616-22-4.mol

Synonyms:200616-22-4;(2S,3S)-3-(dibenzylamino)-4-phenylbutane-1,2-diol;1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-;DTXSID60464583

Chemical Property of 1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 361.204179104
• Heavy Atom Count: 27
• Complexity: 364

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(CO)O)N(CC2=CC=CC=C2)CC3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H]([C@@H](CO)O)N(CC2=CC=CC=C2)CC3=CC=CC=C3

Technology Process of 1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-

There total 7 articles about 1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)- 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: 88.0%

(4S,1'S)-4-[1'-(dibenzylamino)-2'-(phenyl)ethyl]-2,2-dimethyl-1,3-dioxolane → (2S,3S)-3-N,N-dibenzylamino-4-phenylbutane-1,2-diol (200616-22-4)

Guidance literature:

With hydrogenchloride; In acetonitrile; for 1h; Heating;

DOI:10.1021/ol047785o

Reference yield:

(3S)-3-(N,N-dibenzyl)amino-1-hydroxy-1-methylthio-2-oxo-4-phenylbutane (189562-37-6) → (2S,3S)-3-N,N-dibenzylamino-4-phenylbutane-1,2-diol (200616-22-4) + (2R,3S)-3-dibenzylamino-5-phenylbutane-1,2-diol (200616-26-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.833333h;

DOI:10.1016/j.tetlet.2005.06.134

Reference yield:

N,N-dibenzyl-3(S)-amino-1,2(S)-epoxy-4-phenylbutane (127927-43-9) → (2S,3S)-3-N,N-dibenzylamino-4-phenylbutane-1,2-diol (200616-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

2: 88 percent / HCl / acetonitrile / 1 h / Heating

With hydrogenchloride; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile;

DOI:10.1021/ol047785o

upstream raw materials:

(2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol

(3S)-3-(N,N-dibenzyl)amino-1-hydroxy-1-methylthio-2-oxo-4-phenylbutane

(3S)-3-(N,N-dibenzyl)amino-1-methylsulfinyl-2-oxo-4-phenylbutane

N,N-dibenzyl-L-phenylalanine benzyl ester

Downstream raw materials:

(2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol

(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid

(2S,3S)-3-amino-4-phenylbutane-1,2-diol