3-Pentanone, 2-methyl-1-(phenylmethoxy)-, (R)-

Base Information

• Chemical Name: 3-Pentanone, 2-methyl-1-(phenylmethoxy)-, (R)-
• CAS No.: 116652-75-6
• Molecular Formula: C13H18O2
• Molecular Weight: 206.285
• Mol file: 116652-75-6.mol

Synonyms:

Chemical Property of 3-Pentanone, 2-methyl-1-(phenylmethoxy)-, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Pentanone, 2-methyl-1-(phenylmethoxy)-, (R)-

There total 13 articles about 3-Pentanone, 2-methyl-1-(phenylmethoxy)-, (R)- 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: 96.0%

[(S)-3-Benzyloxy-1-ethyl-2-methyl-prop-(Z)-ylidene]-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine → (R)-1-(benzyloxy)-2-methylpentan-3-one (116652-75-6)

Guidance literature:

With ozone; In dichloromethane; at -78 ℃;

DOI:10.1021/ol0256116 DOI:10.1002/1521-3765(20020916)8:18<4272::AID-CHEM4272>3.0.CO;2-K

Reference yield: 92.0%

ethylmagnesium bromide (925-90-6) + (2R)-3-benzyloxy-N-methoxy-N-methyl-2-methylpropanamide (116652-76-7) → (R)-1-(benzyloxy)-2-methylpentan-3-one (116652-75-6)

Guidance literature:

ethylmagnesium bromide; (2R)-3-benzyloxy-N-methoxy-N-methyl-2-methylpropanamide; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1016/j.tet.2011.09.012

Reference yield:

2-((benzyloxy)methyl)pent-1-en-3-one → (R)-1-(benzyloxy)-2-methylpentan-3-one (116652-75-6)

Guidance literature:

With glucose dehydrogenase; D-glucose; nicotinamide adenine dinucleotide phosphate; ene reductase from Bacillus subtilis (EC: 1.6.99.1); In 2-methyltetrahydrofuran; aq. phosphate buffer; at 37 ℃; for 4h; pH=7; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/anie.202103406

upstream raw materials:

ethylmagnesium bromide

(R)-3-benzyloxy-2-methylpropanal

3-Benzyloxy-N-methoxy-2,N-dimethyl-propionamide

Benzyloxymethyl chloride

Downstream raw materials:

(2R,4R,5S)-1-Benzyloxy-5-hydroxy-2,4-dimethyl-heptan-3-one

(2R,4S,5R)-1-Benzyloxy-5-hydroxy-2,4-dimethyl-heptan-3-one

(2R,4S,5R)-1-Benzyloxy-5-hydroxy-2,4,6-trimethyl-heptan-3-one

(2R,4S,5R,6S)-1-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-octan-3-one

Refernces

• 1、 Paterson, Ian,Steadman Neé Doughty, Victoria A.,McLeod, Malcolm D.,Trieselmann, Thomas. "Stereocontrolled total synthesis of (+)-concanamycin F: The strategic use of boron-mediated aldol reactions of chiral ketones". . p. 10119 - 10128. Retrieved 2012/01/14.
• 2、 Enders, Dieter,Vicario, Jose L.,Job, Andreas,Wolberg, Michael,Mueller, Michael. "Asymmetric total synthesis of (-)-callystatin A and (-)-20-epi-callystatin A employing chemical and biological methods". . p. 4272 - 4284. Retrieved 2007/10/03.