Shi's ketone

Base Information

• Chemical Name: Shi's ketone
• CAS No.: 69351-19-5
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.271
• Mol file: 69351-19-5.mol

Synonyms:

Chemical Property of Shi's ketone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Shi's ketone

There total 9 articles about Shi's ketone 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: 100.0%

1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose (25018-67-1) → Shi's ketone (69351-19-5,18422-53-2)

Guidance literature:

With sodium hypochlorite; tetrabutylammomium bromide; potassium bromide; 1-methyl-2-azaadamantane-N-oxyl; In dichloromethane; at 0 ℃; for 0.333333h; Product distribution / selectivity;

Reference yield: 100.0%

→ Shi's ketone (69351-19-5,18422-53-2)

Guidance literature:

With trichloroisocyanuric acid; 4-oxa-5-azahomoadamantane; sodium hydrogencarbonate; In dichloromethane; at 0 ℃; for 1.5h;

Reference yield: 95.0%

C12H20O6 (15080-25-8,18422-54-3,18604-28-9,20880-93-7,25018-67-1,83602-34-0) → Shi's ketone (69351-19-5,18422-53-2)

Guidance literature:

With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl; In acetonitrile; at 20 - 50 ℃; for 3h; Sealed tube;

DOI:10.1021/acs.joc.5b01950

upstream raw materials:

1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

D-Fructose

2,2-dimethoxy-propane

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

Downstream raw materials:

1,2:4,5-di-O-isopropylidene-3-C-phenyl-β-D-fructopyranose

1,2;4,5-di-O-isopropylidene-β-D-fructopyranose

C₂₃H₃₀O₆

(5S,8R,9R)-2,2-dimethyl-10-oxo-1,3,6-trioxaspiro[4,5]decane-8,9-diyl diacetate