172854-76-1

Basic information

• Product Name: (4R)-4-hydroxy-3-[(2R)-5-{2-[(1S,2S,4aR,8aR)-1,2,4a-trimethyl-5-methylidenedecahydronaphthalen-1-yl]ethyl}-3,6-dihydro-2H-pyran-2-yl]cyclopent-2-en-1-one
• Synonyms: 172854-76-1; cacospongionolide B
• CAS NO: 172854-76-1
• Molecular Formula: C₂₆H₃₈O₃
• Molecular Weight: 398.5781
• Mol File: 172854-76-1.mol

Chemical Properties

• Boiling Point: 539.5°C at 760 mmHg
• Flash Point: 176.2°C
• Density: 1.09g/cm³
• Vapor Pressure: 6.88E-14mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: (4R)-4-hydroxy-3-[(2R)-5-{2-[(1S,2S,4aR,8aR)-1,2,4a-trimethyl-5-methylidenedecahydronaphthalen-1-yl]ethyl}-3,6-dihydro-2H-pyran-2-yl]cyclopent-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-hydroxy-3-[(2R)-5-{2-[(1S,2S,4aR,8aR)-1,2,4a-trimethyl-5-methylidenedecahydronaphthalen-1-yl]ethyl}-3,6-dihydro-2H-pyran-2-yl]cyclopent-2-en-1-one(172854-76-1)
• EPA Substance Registry System: (4R)-4-hydroxy-3-[(2R)-5-{2-[(1S,2S,4aR,8aR)-1,2,4a-trimethyl-5-methylidenedecahydronaphthalen-1-yl]ethyl}-3,6-dihydro-2H-pyran-2-yl]cyclopent-2-en-1-one(172854-76-1)

Safety Data

• Hazardous Substances Data: 172854-76-1(Hazardous Substances Data)

Upstream product

• 474055-45-3 (+)-2-(furan-3-yl)-5-[2-(1,2,4a-trimethyl-5-methylene-decahydronaphthalen-1-yl)-ethyl]-3,6-dihydro-2H-pyran 
• 474055-41-9 (1-furan-3-yl-but-3-enyloxy)-acetic acid ethyl ester 
• 474055-47-5 (+)-2-[1-(furan-3-yl)-but-3-enyl]oxy-N-methoxy-N-methyl-acetamide 
• 753002-55-0 (-)-1-[1-(furan-3-yl)-but-3-enyl]oxy-but-3-en-2-one 
• 474055-46-4 (+)-[1-(furan-3-yl)-but-3-enyl]oxyacetic acid 
• 199180-20-6 5,8a-dimethyl-3,4,8,8a-tetrahydro-2H-spiro[naphthalene-1,2′-[1,3]dioxolan]-6(7H)-one 
• 144635-05-2 (R)-1-(furan-3-yl)but-3-en-1-ol 
• 498-60-2 furan-3-carboxaldehyde 
• 753002-56-1 C₂₈H₄₀O₄ 
• 753002-49-2 C₂₆H₃₆O₆ 
• 753002-50-5 C₂₆H₃₆O₄ 
• 753002-57-2 C₂₆H₃₈O₄ 
• 753002-51-6 (-)-5-{2-[6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl]-ethyl}-5,6,8a-trimethyl-octahydronaphthalen-1-one 
• 753002-58-3 (-)-2-(furan-3-yl)-5-[2-(1,2,4a-trimethyl-5-methylene-decahydronaphthalen-1-yl)-ethyl]-3,6-dihydro-2H-pyran 

Relevant articles and documents

Total synthesis of (+)-cacospongionolide B

Total synthesis of (+)-cacospongionolide B was achieved. The synthesis involved highly stereoselective C-glycosidation of a glycal derived from D-arabinose with 3-furyl boronic acid in the presence of a palladium catalyst and S-alkyl Suzuki-Miyaura coupling of in situ generated alkylborane prepared by the reaction of vinyl trans-decaMn with alkenyl triflate.

Total syntheses of (+)- and (-)-cacospongionolide B, cacospongionolide E, and related analogues. Preliminary study of structural features acquired for phospholipase A2 inhibition

The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A 2 suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the γ- hydroxybutenolide moiety.

Total syntheses of (+)- and (-)-cacospongionolide B: New insight into structural requirements for phospholipase A2 inhibition

The first total synthesis of the antiinflammatory marine sponge metabolite (+)-cacospongionolide B has been accomplished in 12 linear steps. The pivotal transformations include a three-step sequence coupling the two main regions of the natural product as well as generating the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A2 suggests that cacospongionolide B has an enantiospecific interaction with the enzyme that is independent of the γ-hydroxybutenolide moiety. Copyright