863660-01-9

Upstream product

• 863662-92-4 (-)-2-((2R,6S)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethanol 

Downstream Products

• 863663-09-6 C₇₉H₁₂₈O₁₃Si₃ 
• 863660-76-8 C₇₃H₁₁₄O₁₃Si₂ 
• 863660-58-6 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester 
• 677707-87-8 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester 
• 863660-52-0 2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester 
• 863660-04-2 5-[(E)-3-((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-propenyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one 
• 863662-94-6 (2S,6R)-2-Benzyloxymethyl-6-prop-2-ynyl-tetrahydro-pyran 
• 863662-93-5 (2S,6R)-2-Benzyloxymethyl-6-(3,3-dibromo-allyl)-tetrahydro-pyran 

Relevant academic research and scientific papers

Total Synthesis of (+)-SCH 351448

Total synthesis of SCH 351448 was accomplished employing the ring-closing olefin metathesis reaction for the preparation of the 28-membered macrodiolide. Copyright

Assignment of absolute configuration to SCH 351448 via total synthesis

(Chemical Equation Presented) The synthesis and absolute configuration of SCH 351448, an interesting ionophoric natural product, are reported herein. Mukaiyama aldol-Prins and segment-coupling Prins reactions were employed to construct the constituent tetrahydropyrans of SCH 351448. Efforts to assemble the C2-symmetric core of the natural product by a templated olefin metathesis strategy are described; however, a stepwise fragment assembly was ultimately utilized to complete the target molecule.

Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations

(+)-SCH 351448 (Na+ salt A) was synthesized employing ring-closing olefin metathesis reaction of an open diene diester intermediate for construction of the 28-membered macrodiolide structure. The open diene diester was prepared from the monomeric hydroxy carboxylic acid and two different olefin fragments. The monomeric hydroxy acid was synthesized via Julia-Julia coupling reaction of intermediates derived from the same olefinic fragments. Oxane units in these fragments were prepared by radical cyclization reactions of β-alkoxyacrylates. Analogous SCH 351448 salts incorporating other mono- and divalent cations may be prepared. Under acidic conditions, SCH 351448 (Na+ salt A) was the most stable complex, but SCH 351448 (Ca2+ salt) and (Na+ salt B) appear to be physiologically important species.