205253-57-2

Upstream product

• 123537-84-8 (1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol 
• 158868-62-3 (1S,2S)-1,3-diiodo-1-phenyl-2-phthalimidopropane 
• 10387-40-3 potassium thioacetate 
• 160857-12-5 Thioacetic acid S-[(2R,3S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-3-phenyl-propyl] ester 
• 507-09-5 tiolacetic acid 

Downstream Products

• 205253-58-3 2-((1S,2R)-2-Mercapto-1-mercaptomethyl-2-phenyl-ethyl)-isoindole-1,3-dione 

Relevant academic research and scientific papers

Synthesis of (-)-5-amino-2(3,4-dimethoxyphenyl)-4-phenyl- 1,3-dithiane

The key intermediate of the synthesis, the (1R,2S)-1-phenyl-2-phthalimido-l,3-propanedithiol (5) was prepared from the corresponding (1S, 2S)-diol 1 in a six-step procedure. The absolute configuration of 5 followed from that of 4, which was established by X-ray crystallographic study. In reaction with veratraldehyde dithiol 5 was converted into 1,3-dithiane 6, isolated as a single isomer. The stereochemistry of the dithiane 6 was deduced from NMR spectral data analysis and MM calculations. Hydrazinolysis of 6 resulted in the title dithiane 7.

Reaction of (1S,2S)-2-amino-1-phenyl-1,3-propanediol with thioacids under the Mitsunobu reaction condition

The Mitsunobu thioesterification was applied to the title 2-amino-1,3-propanediol (1). The regio- and stereochemistry of the reaction was investigated in correlation with the nature of substituents attached to the nitrogen.