123185-86-4

Upstream product

• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 23402-69-9 lithium diphenylcuprate 
• 143800-10-6 [(4S,6R)-2,2-Dimethyl-6-((2S,3S)-3-trimethylsilanyl-oxiranyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 
• 143800-13-9 (R)-5-Hydroxy-3-oxo-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester 
• 143827-05-8 (3S,5R)-3,5-Dihydroxy-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester 
• 143800-10-6 C₁₇H₃₂O₅Si 
• 1694-31-1 tert-butyl acetoacetate 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 123284-04-8 (4S,6R)-6-[(E)-4,4-Bis-(4-fluoro-phenyl)-3-(1-methyl-1H-tetrazol-5-yl)-buta-1,3-dienyl]-4-hydroxy-tetrahydro-pyran-2-one 
• 118918-05-1 trans-(4R,6S)-6-[4,4-bis(4-fluorophenyl)-3-(1-methyl-1H-tetrazol-5-yl)-1,3-butadienyl]-tetrahydro-4-hydroxy-2H-pyran-2-one 
• 118845-49-1 trans-6-<4,4-bis(4-fluorophenyl)-3-(1-methyl-1H-tetrazol-5-yl)-1,3-butadienyl>tetrahydro-4-hydroxy-2H-pyran-2-one 
• 91285-73-3 ((4R,6R)-2,2-Dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-acetic acid 
• 123185-93-3 (3R,5R)-3,5-Dihydroxy-7-phenyl-heptanoic acid 
• 86117-01-3 (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one 
• 118845-88-8 cis-2,2-dimethyl-6-(2-phenylethenyl)-1,3-dioxane-4-acetic acid 
• 123185-87-5 tert-butyl (3R,5S)-6-oxo-3,5-dihydroxy-3,5-O-isopropylidenehexanoate 

Relevant academic research and scientific papers

New chiral blocks for introducing the side chain of HMG-CoA reductase inhibitors

A couple of versatile building blocks (8 and 9) of the side chain portion found in many HMG-CoA reductase inhibitors have been prepared. The successful introduction of the side chain to an aromatic ring by 8 or 9 has been demonstrated.

A new synthesis of HMG-CoA reductase inhibitor NK-104 through hydrosilylation-cross coupling reaction

Regioselective hydrosilylation of t-butyl (3R,5S)-3,5-syn-isopropylidenedioxy-6-heptynoate with CLME2SiH and a catalyst t-Bu3P·Pt(CH2=CHSiMe2)2O gives an (E)-vinylsilane which undergoes cross coupling reaction with aryl halide to afford t-butyl (3R,5S,6E)-7-aryl-3,5-syn-isopropylidenedioxy-6-heptenoate, a precursor of a highly potent HMG-CoA reductase inhibitor NK-104.

Synthesis of an artificial HMG-CoA reductase inhibitor NK-104 via a hydrosilylation-cross-coupling reaction

The hydrosilylation of t-butyl (3R,5S)-3,5-isopropylidenedioxy-6-heptynoate with ClMe2SiH and a platinum catalyst, t-Bu3P·Pt(CH2 = CHSiMe2)2O, gave an (E)-vinylsilane in high yield with high regioselectivity. A subsequent cross-coupling reaction with an aryl halide afforded t-butyl (3R,5S,6E)-7-aryl-3,5-isopropylidene-dioxy-6-heptenoate. This sequence was applied to the synthesis of a potent HMC-CoA reductase inhibitor, NK-104.

(2S,3S)-2,3-Epoxy-3-trimethylsilylpropanal as a New Conjunctive Reagent

The title epoxy aldehyde (>98percent ee) has been prepared.Its reactions with nucleophiles afforded the corresponding adducts with a diastereoselectivity up to 86:14.Synthetic versatility of the chiral epoxy silane moiety makes this aldehyde a useful conjunctive reagent.