281667-70-7

Upstream product

• 281667-66-1 (1S,5S)-3-[[(1S,6R)-6-(benzyloxy)-3-cyclohexen-1-yl]oxy]-4H-1,5-benzodithiepine 1,5-dioxide 
• 281667-61-6 (1S,5S)-spiro[1,5-benzodithiepane-3,8'-[7,9]dioxabicyclo[4.3.0]non-3-ene] 1,5-dioxide 

Downstream Products

• 223694-96-0 (1R,3S,4R,6S)-4-Benzyloxy-7-oxa-bicyclo[4.1.0]heptan-3-ol 
• 327993-86-2 ((2S,3R)-3-Benzyloxy-5-hydroxy-tetrahydro-furan-2-yl)-acetaldehyde 
• 327993-87-3 (6Z,3R,4S)-3-benzyloxy-6-hexadecene-1,4-diol 
• 40617-62-7 (-)-2-deoxy-allo-inositol 
• 223694-97-1 (1S,3R,6R)-6-Benzyloxy-cyclohex-4-ene-1,3-diol 
• 223694-98-2 C₂₇H₂₈O₃ 
• 228412-16-6 L-1,2,4-tri-O-benzyl-3-deoxy-chiro-inositol 

Relevant academic research and scientific papers

C2-symmetric bis-sulfoxide: A novel chiral auxiliary for asymmetric desymmetrization of cyclic meso-1,2-diols

A new heterocyclic compound, C2-symmetric bis-sulfoxide 1, has been found to be an efficient chiral auxiliary for asymmetric desymmetrization of cyclic meso-1,2-diols via diastereoselective acetal fission. Both (R,R)- and (S,S)-1 are readily synthesized with high optical purity via asymmetric oxidation of 1,5-benzodithiepan-3-one (2). After acetalization of meso-1,2- diols 6a-e and a mono-TMS ether 6f with this chiral auxiliary 1, the resulting acetals 7a-f were subjected to base-promoted acetal fission upon treatment with potassium hexamethyldisilazide (KHMDS) followed by acetylation or benzylation to give the desymmetrized diol derivatives 8a-f with high diastereoselectivity. The chiral auxiliary 1 is readily removed by acid- promoted hydrolysis and can be recovered without a loss in enantiomeric excess.