205743-80-2

Upstream product

• 67-56-1 methanol 
• 205743-78-8 (1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol 
• 214278-38-3 5,6-exo-(isopropylidenedioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene 

Downstream Products

• 205743-87-9 (1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol 
• 205743-88-0 (3R,4S,5S,6S)-6-hydroxy-4,5-(isopropylidenedioxy)-3-methoxy-2-phenyl-sulfonylcyclohex-1-enecarbaldehyde 

Relevant academic research and scientific papers

One pot michael addition, vinylsulfone isomerization and alkynyl to alkenyl triple bond reduction. Synthesis of a carbasugar related to Rancinamycin III

Cyclobexenylsulfones 2 show a different behaviour in their reactions with Na/MeOH system depending on the nature of protecting groups R. In the case of R= TMS, the observed sequence Michael addition-vinylsulfone isomerization-alkynyl to alkenyl reduction has been used for the synthesis of a carbasugar related to the antibiotic Rancinamycin III.

Enantioselective synthesis of antibiotic (+)-rancinamycin III derivative and two protected carbasugars of the α-D-talo-series from furan

The synthesis of (+)-1, a carbasugar related to rancinamycin III, has been achieved from diene (+)-3 in two steps using as the key step the transformation of alkyne (-)-2, obtained by resolution of alcohol 6, into diene (+)-3 by treatment with Na/MeOH. Moreover, reduction of the carbonyl group in (+)-1 affords diol (+)-19, in which different protection strategies of the hydroxy groups allows one to obtain, selectively, protected derivatives of α-D-carbatalopyranose (+)-4a and its 6-desoxy derivative (+)- 4b to be obtained selectively.