124377-76-0

Upstream product

• 53346-05-7 2-(benzyloxy)propanal 
• 21969-32-4 crotylmagnesium chloride 
• 121408-94-4 (R)-(+)-isobutyl O-benzyllactate 
• 100-39-0 benzyl bromide 
• 35998-93-7 tri-n-butylcrotyltin 
• 53346-05-7 (R)-2-benzyloxypropanal 
• 31197-41-8 crotyltributylstannane 
• 4784-77-4 (E)-1-Bromo-2-butene 

Downstream Products

• 177598-63-9 ((1R,2R,3S)-2-Methoxy-1,3-dimethyl-pent-4-enyloxymethyl)-benzene 
• 177766-57-3 (3S,4S,6S,7S,8R,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-8-methoxy-6-(4-methoxy-benzyloxy)-3,7-dimethyl-dec-1-en-4-ol 
• 177598-72-0 4-[(1E,3E,5E)-(7R,8S,9S,11S,12S)-4-Benzenesulfonyl-7-methoxy-9-(4-methoxy-benzyloxy)-11-methoxymethoxy-2,6,8,12-tetramethyl-tetradeca-1,3,5,13-tetraenyl]-2-methyl-oxazole 
• 177598-70-8 1-[(E)-(1S,2S,3R)-6-Benzenesulfonyl-3-methoxy-1-((2S,3S)-2-methoxymethoxy-3-methyl-pent-4-enyl)-2,4-dimethyl-hex-4-enyloxymethyl]-4-methoxy-benzene 
• 177598-69-5 (3R,4R,5S,6S,8S,9S)-4-Methoxy-6-(4-methoxy-benzyloxy)-8-methoxymethoxy-3,5,9-trimethyl-undeca-1,10-dien-3-ol 
• 177598-68-4 (3R,4S,5S,7S,8S)-3-Methoxy-5-(4-methoxy-benzyloxy)-7-methoxymethoxy-4,8-dimethyl-dec-9-en-2-one 
• 177598-67-3 (3S,4S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-3-(4-methoxy-benzyloxy)-4-methyl-heptanal 

Relevant academic research and scientific papers

Effects of Plefin Geometry on the Stereochemistry of Lewis Acid Mediated Additions of Crotylstannanes to Aldehydes

The role of the double bond geometry (E/Z stereochemistry) in reactions of crotylstannanes with aldehydes has been examined for representative "simple", α-alkoxy, and β-alkoxy aldehydes.For the reaction of crotylstannane with simple achiral aliphatic, aro

Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to a-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems

The couplings of crotyl bromide (1) and 1,3-dibromopropene (2) to a triad of conformationally unrestricted α-oxy aldehydes in water, aqueous THF (1:1), and anhydrous THF are described. In no example involving 1 was the formation of anti.syn product detected. The proportion of syn isomers reached a maximum (syn/anti = 5.6:1) when the neighboring hydroxyl group was unprotected and water was the reaction medium. Although internal chelation also operates to some degree with 2, considerable erosion of this mechanistic pathway (maximum now only 2:1) in favor of Felkin and "anti-Felkin" transition states is reflected in the product distributions. This trend can be synthetically advantageous, and a utilitarian example is demonstrated. The indium reagents studied here are notably efficient nucleophilic reaction partners in water.

Synthetic studies on the rhizoxins. II. An approach to the C10-C26 subunit using 'substrate directed' allylstannane additions to aldehydes

The construction of a C10-C26 fragment of the 16-membered antitumor macrolide rhizoxin has been achieved in an efficient manner. The central portion of this molecule has been prepared in enantiopure form via an iterative allylstannylation protocol starting with the ester of (R)-lactic acid. The oxazole portion of rhizoxin was attached via a samarium diiodide modified Julia coupling to generate the requisite all E triene.