2294-61-3

Basic information

• Product Name: (-)-Ichthyothereol
• Synonyms: (2S)-Tetrahydro-2β-[(E)-1-nonene-3,5,7-triynyl]-2H-pyran-3α-ol;[2S,(-)]-Tetrahydro-2β-[(E)-1-nonene-3,5,7-triynyl]-2H-pyran-3α-ol;Ichthyotherol
• CAS NO: 2294-61-3
• Molecular Formula: C14H14O2
• Molecular Weight: 214.25976
• Mol File: 2294-61-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 326.5°C at 760 mmHg
• Flash Point: 144°C
• Appearance: /
• Density: 1.167g/cm³
• Vapor Pressure: 1.64E-05mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: (-)-Ichthyothereol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Ichthyothereol(2294-61-3)
• EPA Substance Registry System: (-)-Ichthyothereol(2294-61-3)

Safety Data

• Hazardous Substances Data: 2294-61-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H14O2/c1-2-3-4-5-6-9-12-11(13)8-7-10-14-12/h6,9,11-13H,7-8,10H2,1H3/b9-6+/t11-,12+/m1/s1

Upstream product

• 362675-47-6 (2S,3R)-(-)-3-(tert-butyldimethylsiloxy)-2-[(E)-2-iodovinyl]tetrahydropyran 
• 362675-46-5 (2S,3R)-(-)-3-(tert-butyldimethylsiloxy)-2-ethynyltetrahydropyran 
• 362675-52-3 (2S,3R)-(-)-3-(tert-butyldimethylsiloxy)-2-[(1E)-non-3,5,7-triyn-1-enyl]tetrahydropyran 

Downstream Products

• 692-94-4 (E)-Dec-2-ene-4,6,8-triynoic acid methyl ester 

Relevant articles and documents

First total synthesis of (-)-ichthyothereol and its acetate

The first and stereoselective total syntheses of (-)-ichthyothereol (1) and its acetate ((+)-2) were achieved by incorporation of the two chiral centers of diethyl L-tartrate. The starting diethyl L-tartrate was converted into trans-2-ethynyl-3-hydroxytetrahydropyran 14 in a stereoselective manner via the endo mode cyclization of the epoxy-alkyne derivative 12. The alcohol 12 was then transformed into (E)-iodoolefin derivative 15, which was exposed to a coupling reaction with 1-tributylstannyl-1,3,5-heptyne (19), derived from the corresponding 1-trimethylsilyl-1,3,5-heptyne (18), under Stille conditions to produce the all-carbon framework of the target natural products. Chemical modification of the coupled product 20 under conventional conditions completed the first total synthesis of (-)-ichthyothereol (1) and its acetate ((+)-2).