(3R)-3,4-bis(phenylmethoxy)butan-2-one

Base Information

• Chemical Name: (3R)-3,4-bis(phenylmethoxy)butan-2-one
• CAS No.: 94278-74-7
• Molecular Formula: C18H20O3
• Molecular Weight: 284.355
• DSSTox Substance ID: DTXSID101282826
• Nikkaji Number: J2.834.381G
• Mol file: 94278-74-7.mol

Synonyms:94278-74-7;DTXSID101282826;(3R)-3,4-Bis(phenylmethoxy)-2-butanone

Chemical Property of (3R)-3,4-bis(phenylmethoxy)butan-2-one

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 284.14124450
• Heavy Atom Count: 21
• Complexity: 291

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C(COCC1=CC=CC=C1)OCC2=CC=CC=C2
• Isomeric SMILES: CC(=O)[C@@H](COCC1=CC=CC=C1)OCC2=CC=CC=C2

Technology Process of (3R)-3,4-bis(phenylmethoxy)butan-2-one

There total 8 articles about (3R)-3,4-bis(phenylmethoxy)butan-2-one 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:

(E)-(2S,5S)-1-Benzyloxy-3,5-dimethyl-hept-3-ene-2,6-diol (132409-34-8,132409-43-9,132488-13-2,132488-17-6) → (R)-3,4-bis(benzyloxy)butan-2-one (94278-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / KOH, TDA-1 / benzene

2: 1. O₃, dimethyl sulfide, 2. lithium tris(1,1-diethylpropyloxy)aluminum hydride / 1. CH₂Cl₂, 0.5h, -78 deg C, 2. THF, 15min

With potassium hydroxide; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; dimethylsulfide; ozone; In benzene;

DOI:10.1021/jo00006a049

Reference yield:

(1RS,4'R)-1-<2',2'-Dimethyl-1',3'-dioxolan-4'-yl>aethanol (74183-62-3) → (R)-3,4-bis(benzyloxy)butan-2-one (94278-74-7)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.02.012

Reference yield:

C30H36O3 (132488-16-5) → (R)-3,4-bis(benzyloxy)butan-2-one (94278-74-7) + (2R,3S)-(+)-2-methyl-1,3-butanediol 3-benzylether (121404-74-8)

Guidance literature:

With lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; dimethylsulfide; ozone; Yield given. Multistep reaction. Yields of byproduct given; 1. CH₂Cl₂, -78 deg C, 0.5h, 2. THF, 15min;

DOI:10.1021/jo00006a049

upstream raw materials:

C₃₀H₃₆O₃

C₃₀H₃₆O₃

C₃₀H₃₆O₃

benzyl bromide

Downstream raw materials:

(S)-N-[3,4-bis(benzyloxy)butan-2-ylidene]-1-phenylmethanamine

(2S,3S)-N-benzyl-3,4-bis(benzyloxy)butan-2-amine

(2R,3S)-N-benzyl-3,4-bis(benzyloxy)butan-2-amine