Synthesis of 2-substituted 5,7,8-trimethyl-6-hydroxythiochromans and purported syntheses of sulfur-containing analogues of vitamin E

Download
  1. Get@NRC: Synthesis of 2-substituted 5,7,8-trimethyl-6-hydroxythiochromans and purported syntheses of sulfur-containing analogues of vitamin E (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1021/jo00360a013
AuthorSearch for: ; Search for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titleJournal of Organic Chemistry
ISSN0022-3263
Volume51
Issue10
Pages17001704; # of pages: 5
Subject1 thia alpha tocopherol; 2,2,5,7,8 pentamethylthiochroman 6 ol; 2,5,7,8 tetramethylthiochroman 6 ol; 5,7,8 trimethylthiochroman 6 ol; drug analysis; drug identification; drug synthesis; gas chromatography; mass spectrometry; nonhuman; nuclear magnetic resonance; theoretical study; thin layer chromatography
AbstractThe syntheses of 5,7,8-trimethyl-, 2,5,7,8-tetramethyl-, and 2,2,5,7,8-pentamethyl-6-hydroxythiochromans have been achieved by a Michael-type condensation of methyl acrylate and related methyl esters with 2,3,5-trimethyl-4-hydroxythiochromans followed by cyclization of the free acid and reduction. These three previously unknown compounds can serve as simple models for the still unknown 1-thia-α-tocopherol (1), which could not be prepared by this route. Indeed, two purported syntheses of 18,9 have been shown to yield an essentially identical mixture of five isomers of the desired compound. For three components in this mixture, including the two major products, it is highly probable that the initial condensation at sulfur has not been followed by ring closure.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276636
Export citationExport as RIS
Report a correctionReport a correction
Record identifier3bbd8af4-f14e-41cf-bab5-0e09510b279f
Record created2015-10-13
Record modified2016-05-09
Bookmark and share
  • Share this page with Facebook (Opens in a new window)
  • Share this page with Twitter (Opens in a new window)
  • Share this page with Google+ (Opens in a new window)
  • Share this page with Delicious (Opens in a new window)