118207-58-2

Upstream product

• 218434-91-4 5-(4-Methoxy-benzyloxy)-pent-2-ynoic acid methyl ester 
• 105-13-5 4-Methoxybenzyl alcohol 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 128685-08-5 C₈₂H₁₄₉NO₁₂S₂Si₃ 
• 128685-08-5 C₈₂H₁₄₉NO₁₂S₂Si₃ 
• 128684-93-5 <1(1R,3R,4R),1E,3S,4S,5S,7S,7(4R)>-2,4-dimethyl-3-hydroxy-7-<2-(iodomethyl)tetrahydrofuran-4-yl>-7-<(4-methoxybenzyl)oxy>-1-<3-methoxy-4-<(triisopropylsilyl)oxy>cyclohex-1-yl>-5-<(triisopropylsilyl)oxy>-1-heptene 
• 128684-93-5 <1(1R,3R,4R),1E,3R,4S,5S,7S,7(4R)>-2,4-dimethyl-3-hydroxy-7-<2-(iodomethyl)tetrahydrofuran-4-yl>-7-<(4-methoxybenzyl)oxy>-1-<3-methoxy-4-<(triisopropylsilyl)oxy>cyclohex-1-yl>-5-<(triisopropylsilyl)oxy>-1-heptene 
• 128684-95-7 C₅₈H₁₀₂INO₁₀Si₂ 
• 128684-96-8 <1(1R,3R,4R),1E,3(2S),3S,4S,5S,7S,8R>-3--2,4-dimethyl-8-(hydroxymethyl)-7-<(4-methoxybenzyl)oxy>-1-<3-methoxy-4-<(triisopropylsilyl)oxy>cyclohex-1-yl>-5-<(triisopropylsilyl)oxy>-1,10-undecadiene 
• 128684-97-9 <1(1R,3R,4R),1E,3(2S),3S,4S,5S,7S,8S>-3--7-<(4-methoxybenzyl)oxy>-1-<3-methoxy-4-<(triisopropylsilyl)oxy>cyclohex-1-yl>-2,4-dimethyl-8-(2-propen-1-yl)-5-<(triisopropylsilyl)oxy>-1-nonen-9-al 
• 128708-25-8 <2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal 
• 128684-92-4 <3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene 
• 118207-54-8 (3S,4S,5S,7S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-7-(4-methoxy-benzyloxy)-4-methyl-hept-1-en-3-ol 
• 118207-54-8 (3R,4S,5S,7S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-7-(4-methoxy-benzyloxy)-4-methyl-hept-1-en-3-ol 
• 118207-55-9 (2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal 
• 122948-79-2 (2R,3S,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-5-(4-methoxy-benzyloxy)-2-methyl-pentanal 
• 118207-56-0 (4R,5R,6R)-6-[(S)-2-((R)-5-Iodomethyl-tetrahydro-furan-3-yl)-2-(4-methoxy-benzyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxane-4-carbaldehyde 

Relevant academic research and scientific papers

ENANTIOSELECTIVE CROSS DEHYDROGENATIVE COUPLING REACTIONS AND COMPOUNDS SYNTHESIZED BY THE REACTIONS

Disclosed are enantioselective cross dehydrogenative coupling reactions for synthesizing tetrahydropyran compounds. Novel tetrahydropyran compounds may be synthesized by the disclosed methods as well as tetrahydropyran precursor compounds for synthesizing various naturally occurring compounds. The enantioselective cross dehydrogenative coupling reactions utilize in situ Lewis Acid activation in combination with oxidative formation of an oxocarbenium ion to provide a highly efficient and selective coupling reaction for synthesizing tetrahydropyran compounds.

An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans

An enantioselective cross-dehydrogenative coupling (CDC) reaction to access tetrahydropyrans has been developed. This process combines in situ Lewis acid activation of a nucleophile in concert with the oxidative formation of a transient oxocarbenium electrophile, leading to a productive and highly enantioselective CDC. These advances represent one of the first successful applications of CDC for the enantioselective couplings of unfunctionalized ethers. This system provides efficient access to valuable tetrahydropyran motifs found in many natural products and bioactive small molecules.

Synthesis of the C(1)-C(18) segment of lophotoxin and pukalide. Control of 2-alkenylfuran (E/Z)-configuration.

[reaction: see text] The convergent synthesis of the fully functionalized C(1)-C(18) segment 24 of the furanocembranes lophotoxin and pukalide was accomplished in 11 steps and 10% overall yield. The key step was a stereoselective conversion of alkynoate 2