(1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one

Base Information

• Chemical Name: (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one
• CAS No.: 618387-07-8
• Molecular Formula: C₁₆H₁₆O₄
• Molecular Weight: 272.301
• Mol file: 618387-07-8.mol

Synonyms:(1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one

Chemical Property of (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one

There total 3 articles about (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[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: 51.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one (618387-07-8)

Guidance literature:

Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -30 ℃; for 0.5h; Inert atmosphere;

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo801190m

Reference yield:

(1R,2R,3R,5S)-3-benzoyloxy-2-vinyl-bicyclo[3.2.0]heptan-6-one (618386-93-9) → (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one (618387-07-8) + Benzoic acid (3aR,4R,5R,6aS)-1-oxo-4-vinyl-hexahydro-cyclopenta[c]furan-5-yl ester

Guidance literature:

With dihydrogen peroxide; In 2,2,2-trifluoroethanol; at 5 ℃;

DOI:10.1016/S0040-4020(03)00920-7

Reference yield:

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1) → (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one (618387-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

2: KOtBu / tetrahydrofuran

With potassium tert-butylate; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Dess-Martin oxidation / 2: Wittig olefination;

DOI:10.1016/j.tetlet.2006.06.140

upstream raw materials:

(1R,2R,3R,5S)-3-benzoyloxy-2-vinyl-bicyclo[3.2.0]heptan-6-one

Methyltriphenylphosphonium bromide

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Downstream raw materials:

benzoic acid 4-(3-hydroxy-3-methyloct-1-enyl)-2-oxo-hexahydrocyclopenta[b]furan-5-yl ester

dinoprost