220564-16-9

Upstream product

• 1335101-41-1 (3E,5E)-(1Ss)-(p-tolylsulfinyl)hepta-3,5-dien-2-one 
• 1335101-40-0 (S,3E,5E)-1-((S)-p-tolylsulfinyl)hepta-3,5-dien-2-ol 
• 100-39-0 benzyl bromide 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 220564-13-6 (1S,2S,3R,6R)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 
• 220564-15-8 (1R,4R,5S,6R)-4,5,6-trihydroxycyclohex-2-en-1-yl pivalate 
• 800408-98-4 (1S,4S,5S,6S)-4,5,6-tris(benzyloxy)cyclohex-2-enol 
• 671199-46-5 (4R,5S,6R)-4,5,6-tris(benzyloxy)cyclohex-2-en-1-one 
• 382601-71-0 (-)-(1R,2R,3S,4R)-1-pivaloxy-2,3,4-tribenzyloxy-5-cyclohexene 

Downstream Products

• 197896-26-7 1D-4,5,6-tri-O-benzyl-2,3-dideoxy-myo-inositol 
• 801297-68-7 1D-2,3-anhydro-4,5,6-tri-O-benzyl-myo-inositol 
• 176380-10-2 (1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol 
• 1053641-05-6 Phosphoric acid benzyl ester (R)-2-benzyloxy-3-hexadecyloxy-propyl ester (1R,2R,3S,4R)-2,3,4-tris-benzyloxy-cyclohexyl ester 
• 197896-27-8 Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R)-2,3,4-tris-benzyloxy-cyclohexyl ester 

Relevant academic research and scientific papers

Stereoselective Formal Synthesis of (+)- and (-)-Cyclophellitol and (-)-Conduritol-B and Synthesis of (-)-Conduramine-B Derivative Using a Sulfinyl Moiety for C-O Bond Formation and α-Chloro Sulfide for C-C Bond Formation

The formal total synthesis of both the enantiomers of cyclophellitol and conduritol-B and synthesis of conduramine-B derivative have been achieved from a common intermediate, obtained by regio- and stereoselective vicinal functionalization of a diene utilizing an intramolecular sulfinyl group as a nucleophile, followed by stereoselective preparation of an allylic sulfide by reaction of vinylzinc bromide with an electrophilic α-chloro sulfide, and last by ring-closing metathesis reaction as the key steps. The sulfoxide, sulfilimine, and sulfur ylid prepared from this common intermediate have been transformed into derivatives of conduritol-B, conduramine-B, and (-)-cyclophellitol, respectively. The silyl sulfide was converted via sila-Pummerer rearrangement, hydrolysis, and reduction in an one-pot operation to a hydroxymethyl group. [2,3]-Wittig-Still rearrangement was employed for the synthesis of (+)-cyclophellitol. The potential utility of sulfur intermediates as nucleophilic and electrophilic partners in total synthesis is elegantly demonstrated.

Synthesis of anti-tumour phosphatidylinositol analogues from glucose by the use of ring-closing olefin metathesis

A divergent strategy is described for synthesis of the novel phosphatidylinositols 1-3. The synthetic approach commences from benzyl-protected methyl 6-iodo-6-deoxy-α-D-glucopyranoside, which undergoes zinc-mediated reductive fragmentation followed by vin

AAA in KAT/DYKAT processes: First- and second-generation asymmetric syntheses of (+)- and (-)-cyclophellitol

Kinetic resolutions and kinetic asymmetric transformations (KAT) as well as dynamic kinetic resolutions and dynamic kinetic asymmetric transformations (DYKAT) are important synthetic protocols. The feasibility of KAT and DYKAT processes for asymmetric all

Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol

Enantiomerically pure (+)-cyclophellitol is readily available from benzoquinone employing an asymmetric palladium catalyzed kinetic resolution of racemic conduritol B and a novel easily cleavable pivalate analogue.