144401-72-9

Basic information

• Product Name: (8S)-8-(p-tolylsulfonyloxy)-<8-(2)H>octanoic acid
• CAS NO: 144401-72-9
• Molecular Weight: 315.395
• Mol File: 144401-72-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (8S)-8-(p-tolylsulfonyloxy)-<8-(2)H>octanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (8S)-8-(p-tolylsulfonyloxy)-<8-(2)H>octanoic acid(144401-72-9)
• EPA Substance Registry System: (8S)-8-(p-tolylsulfonyloxy)-<8-(2)H>octanoic acid(144401-72-9)

Safety Data

• Hazardous Substances Data: 144401-72-9(Hazardous Substances Data)

Upstream product

• 14113-02-1 ethyl 8-chloro-8-oxooctanoate 
• 14113-01-0 Ethyl hydrogen suberate 
• 2050-23-9 diethyl suberate 
• 1393604-36-8 C₁₀H₁₉⁽²⁾HO₃ 
• 144401-69-4 ethyl 8-hydroxy-<8,8-(2)H2>octanoate 
• 144401-70-7 ethyl 7-(<(2)H>formyl)heptanoate 
• 505-48-6 octane-1,8-dioic acid 
• 144401-82-1 (8S)-8-hydroxy-<8-(2)H>octanoic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant articles and documents

Synthesis of Linoleic Acid with Chiral Isotopic Labelling at a Flanking and a Medial Allylic Methylene: the (8R,9Z,12Z)- and (11R,9Z,12Z)--Stereoisomers, and (Z)-Non-3-enal

-Oct-2-ynal is converted by fermenting bakers' yeast into (1S)-oct-2-yn-1-ol with an enantiomeric purity of >96percent as measured by Mosher's MTPA method.The alcohol, as its tosyl ester, was then converted by copper-catalysed coupling with the di-Grignard of dec-9-ynoic acid and catalytic semi-hydrogenation, into (11R)-linoleic acid having less than 2percent E-material and >95 atom percentD.Provision for (11S)-linoleic acid was made by configurational inversion of (1R)-oct-2-yn-1-ol using Mitsunobu chemistry.(8R)-Linoleic acid is made by a similar approach, the labelled chiral centre being formed on (8S)-8-hydroxy-octanoic acid (>96percent ee).Reaction of the corresponding tosate with lithium acetylide-ethylenediamine complex gave, with configurational inversion, (8R)-dec-9-ynoic acid, built into (8R)-linoleic acid.A degradative circuit is applied to estimate the extent of configurational inversion in the displacement.Mitsunobu inversion of the (8S)-8-hydroxy compound provides access to (8S)-linoleic acid. (Z)-Non-3-enal, a labile aldehyde from the enzymic degradation of linoleic acid, is made in -labelled form by a synthesis which uses, as a key step, the reaction between triheptynylborane and deuteriodiazoacetic ester.