(1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one

Base Information

• Chemical Name: (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one
• CAS No.: 476153-93-2
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.225
• Mol file: 476153-93-2.mol

Synonyms:(1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one

Chemical Property of (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one

There total 20 articles about (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-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: 90.0%

carbon monoxide (201230-82-2) + (1R,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol (476153-91-0) → (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one (476153-93-2)

Guidance literature:

With sodium acetate; acetic acid; copper dichloride; palladium dichloride; at 20 ℃; for 10h;

DOI:10.1016/j.tet.2005.01.004

Reference yield: 85.0%

(1S,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol (476153-92-1) → (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one (476153-93-2)

Guidance literature:

(1S,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol; With copper diacetate; lithium chloride; In acetic acid; at 20 ℃; for 0.166667h; Sealed tube;

With dichloro bis(acetonitrile) palladium(II); iron pentacarbonyl; In acetic acid; at 60 ℃;

DOI:10.1055/s-0033-1340619

Reference yield: 78.0%

(5R)-5-[(1R,2R)-1-(tert-butyldimethylsilyloxy)-2-hydroxy-2-phenylethyl]-5H-furan-2-one (677300-94-6) → (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one (476153-93-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo0356356

upstream raw materials:

carbon monoxide

(1R,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol

(5R)-5-[(1R,2R)-1-(tert-butyldimethylsilyloxy)-2-hydroxy-2-phenylethyl]-5H-furan-2-one

(4S,4'R,5R)-2,2,2',2'-tetramethyl-5-vinyl-4,4'-bi(1,3-dioxolane)

Downstream raw materials:

methyl 3-([2S,3S,4R,5R]-3,4-dihydroxy-5-phenyltetrahydrofuran-2-yl)propionate

3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid