155326-45-7

Basic information

• Product Name: Pyrenophorol [HelMidiol]
• Synonyms: Helmidiol
• CAS NO: 155326-45-7
• Molecular Formula: C16H24O6
• Molecular Weight: 312.3582
• Mol File: 155326-45-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 131℃
• Boiling Point: 585.4°Cat760mmHg
• Flash Point: 214.2°C
• Appearance: /
• Density: 1.117g/cm³
• Vapor Pressure: 3.85E-16mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: Pyrenophorol [HelMidiol](CAS DataBase Reference)
• NIST Chemistry Reference: Pyrenophorol [HelMidiol](155326-45-7)
• EPA Substance Registry System: Pyrenophorol [HelMidiol](155326-45-7)

Safety Data

• Hazardous Substances Data: 155326-45-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H24O6/c1-11-3-5-13(17)8-10-16(20)22-12(2)4-6-14(18)7-9-15(19)21-11/h7-14,17-18H,3-6H2,1-2H3/b9-7-,10-8+

Upstream product

• 80708-19-6 5,14-Dimethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione 
• 58917-26-3 (S)-sulcatol 
• 1373756-63-8 (3S,6S)-6-tert-butyldiphenylsilyloxyhept-1-en-3-ol 
• 4630-06-2 6-methylhept-5-en-2-ol 
• 110-93-0 6-Methyl-hept-5-en-2-on 

Relevant articles and documents

Stereoselective total synthesis of (-)-(5S,8R,13S,16R)-pyrenophorol

The total synthesis of 16-membered C2-symmetric dilactone (-)-(5S,8R,13S,16R)-pyrenophorol was accomplished starting from enantiomerically pure propylene oxide prepared by hydrolytic kinetic resolution of (±)-propylene oxide with key steps of cross-metathesis and intermolecular Mitsunobu cyclization for the construction of macrolactone.

An alternative stereoselective total synthesis of (-)-pyrenophorol

The total synthesis of 16-membered C2–Symmetric dilactone (-)-Pyrenophorol was accomplished starting from commercially available (S)-epoxide prepared by hydrolytic kinetic resolution of (±)–epoxide with key steps of Grignard reaction, Swern oxidation, Wittig reaction and cyclization was achieved by intermolecular Mitsunobu cyclization. The synthesis of (-)-Pyrenophorol accomplished from cheaply available starting material, easily work-up procedures and reduction of cost in industrial process were major advantages of this route.

Asymmetric hydroformylation-initiated tandem sequences for syntheses of (+)-patulolide C, (-)-pyrenophorol, (+)-decarestrictine L, and (+)-prelog djerassi lactone

Four different Rh-catalyzed asymmetric hydroformylation (AHF) tandem reactions have been developed in the context of the total syntheses of (+)-patulolide C, (-)-pyrenophorol, (+)-decarestrictine L, and (+)-Prelog-Djerassi lactone. A total synthesis of (+)-patulolide C has been accomplished in three steps utilizing a Rh(I)-catalyzed Z-selective anti-Markovnikov hydroacetoxylation of a known alkyne to give a Z-enol acetate with excellent selectivity. An AHF/intramolecular Wittig olefination cascade was utilized to set the C4-hydroxyl stereochemistry, E-olefin geometry, and form the macrolactone. In addition, both (-)-pyrenophorol and (+)-decarestrictine L have been synthesized from the enantiomeric (4R)- and (4S)-4-(tert-butyldimethylsiloxy)-1-pentyne in five and four steps, respectively. These syntheses feature Ru(II)-catalyzed Z-selective anti-Markovnikov hydroacetoxylation of terminal alkynes followed by AHF/Wittig olefination sequences to rapidly establish functionality and stereogenicity. A synthesis of (+)-Prelog-Djerassi lactone was accomplished in three isolations from the known 1-vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]-octane ortho ester. An AHF/crotylation tandem sequence has been developed to set the C2-C4 stereochemistry. An asymmetric hydrogenation was employed to set the C6 stereochemistry, resulting in an especially efficient enantioselective synthesis from achiral starting material. In summary, these syntheses have greatly improved efficiency in terms of atom-economy, catalytic stereoselective transformations, inexpensive reagents, step-counts, and overall yield when compared with previous synthetic attempts.