89307-16-4Relevant academic research and scientific papers
Stereoselective Syntheses of Lignin Model Compounds of the β-0-4 and β-1 Types
Ahvonen, Toivo,Brunow, Goesta,Kristersson, Per,Lundquist, Knut
, p. 845 - 850 (2007/10/02)
The preparation of erythro forms of lignin model compounds of the β-0-4 type by hydroboration of α-aryloxycinnamic acids, using a borate dimethyl sulfide complex as a reagent, has been studied.The erythro form of 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol was obtained in a yeild of about 50percent.Acid-catalyzed rearangements of chalcone oxides result in the formation of α-formyldesoxibenzoins which give 1,2-diaryl-1,3-propanediols on borohydride reduction.The synthesis of the erythro forms of 1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol and 1,2-bis(4-hydroxy-3,5-dimethoxyphenyl)-1,3-propanediol by this reaction route is discribed; 1,2-diaryl-1,3-propanediols represent lignin model compounds for the β-1 type of structure.
