2-Oxocanone, 8-methyl-4-(phenylmethoxy)-, (4S,8R)-

Base Information

• Chemical Name: 2-Oxocanone, 8-methyl-4-(phenylmethoxy)-, (4S,8R)-
• CAS No.: 213818-72-5
• Molecular Formula: C15H20O3
• Molecular Weight: 248.322
• Mol file: 213818-72-5.mol

Synonyms:

Chemical Property of 2-Oxocanone, 8-methyl-4-(phenylmethoxy)-, (4S,8R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxocanone, 8-methyl-4-(phenylmethoxy)-, (4S,8R)-

There total 13 articles about 2-Oxocanone, 8-methyl-4-(phenylmethoxy)-, (4S,8R)- 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: 77.0%

(3S,7R)-3-(benzyloxy)-7-hydroxyoctanoic acid (213818-71-4) → (4S,8R,12S,16R)-4,12-dibenzyloxy-8,16-dimethyl-1,9-dioxacyclohexadecane-2,10-tetron + (4S,8R)-4-(benzyloxy)-8-methyloxocan-2-one (213818-72-5)

Guidance literature:

With hafnium(IV) trifluoromethanesulfonate; 4-(trifluoromethyl)benzoic anhydride; In tetrahydrofuran; acetonitrile; for 8h; Heating;

DOI:10.1246/cl.1998.831

Reference yield: 69.0%

(3S,7R)-3-(benzyloxy)-7-hydroxyoctanoic acid (213818-71-4) → (4S,8R)-4-(benzyloxy)-8-methyloxocan-2-one (213818-72-5)

Guidance literature:

(3S,7R)-3-(benzyloxy)-7-hydroxyoctanoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere;

With dmap; In toluene; at 90 - 100 ℃; for 10h; stereoselective reaction; Inert atmosphere;

DOI:10.1007/s00706-015-1526-4

Reference yield:

(5R,2E)-5-(tert-butyl-dimethyl-silyloxy)-hex-2-enoic acid ethyl ester (154568-30-6) → (4S,8R)-4-(benzyloxy)-8-methyloxocan-2-one (213818-72-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / hydrogen / palladium on activated carbon / ethanol / 10 h / 20 °C

2: 90 percent / DIBAL / toluene / 2 h / -78 °C

3: 89 percent / tin(II) trifluoromethanesulfonate; tributyltin fluoride; chiral diamine deriv. of D-proline / CH₂Cl₂ / 3 h / -78 °C

4: 93 percent / N,N-diisopropylethylamine; silver trifluoroacetate / methanol / 10 h / 20 °C

5: trifluoromethanesulfonic acid / CH₂Cl₂ / 0.5 h / 20 °C

6: aq. potassium hydroxide / methanol / 3 h / 20 °C

7: hafnium tetrakis(trifluoromethanesulfonate); 4-trifluoromethylbenzoic anhydride / acetonitrile / 2 h / Heating

With potassium hydroxide; tin(II) trifluoromethanesulfonate; hafnium tetrakis(trifluoromethanesulfonate); trifluorormethanesulfonic acid; chiral diamine deriv. of D-proline; 4-(trifluoromethyl)benzoic anhydride; hydrogen; silver trifluoroacetate; diisobutylaluminium hydride; tributyltin fluoride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; toluene; acetonitrile; 1: Catalytic hydrogenation / 2: Reduction / 3: aldol reaction / 4: transesterification / 5: Etherification / 6: Hydrolysis / 7: Cyclization;

DOI:10.3987/COM-99-S85

upstream raw materials:

(3S,7R)-3-(benzyloxy)-7-hydroxyoctanoic acid

(5R,2E)-5-(tert-butyl-dimethyl-silyloxy)-hex-2-enoic acid ethyl ester

(-)-(5R)-5-(tert-butyldimethylsilyloxy)-hexanal

ethyl (5R)-5-[(tert-butyldimethylsilyl)oxy]hexanoate

Refernces

• 1、 Shiina, Isamu,Fujisawa, Hidehiko,Ishii, Toshihiro,Fukuda, Yoshio. "Stereoselective total synthesis of cephalosporolide D". . p. 1105 - 1123. Retrieved 2007/10/03.