410095-19-1

Upstream product

• 86-93-1 1-Phenyl-1H-tetrazole-5-thiol 
• 289472-96-4 (2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-methanol 
• 66335-71-5 (S)-4-methyl-1-trityloxymethyl-3,6-dihydro-2H-pyran 
• 302554-87-6 (S)-2-allyloxy-4-methyl-1-trityloxy-4-pentene 
• 1315319-05-1 (S)-1-((4-methoxybenzyl)oxy)-4-methylpent-4-en-2-ol 
• 372511-49-4 1-((S)-2-Allyloxy-4-methyl-pent-4-enyloxymethyl)-4-methoxy-benzene 
• 302554-94-5 (2S)-2-(4-methoxybenzyloxy)-4-methyl-3,6-dihydro-2H-pyran 

Downstream Products

• 410095-15-7 (S)-5-[(4-methyl-3,6-dihydro-2H-pyran-2-yl)methylsulfonyl]-1-phenyl-1H-tetrazole 
• 410095-20-4 5-(6-methyl-3,7-dioxa-bicyclo[4.1.0]hept-4-ylmethanesulfonyl)-1-phenyl-1H-tetrazole 
• 410095-22-6 (2E,7E)-(5R,6S)-5-(4-Methoxy-benzyloxy)-8-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-triisopropylsilanyloxy-octa-2,7-dien-1-ol 
• 410095-25-9 (E)-(5R,6S)-5-(4-Methoxy-benzyloxy)-8-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-triisopropylsilanyloxy-oct-7-en-2-yn-1-ol 
• 410095-26-0 {(2S,3S)-3-[(E)-(2R,3S)-2-(4-Methoxy-benzyloxy)-5-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-3-triisopropylsilanyloxy-pent-4-enyl]-oxiranyl}-methanol 
• 410095-21-5 (S)-2-[(E)-(3S,4R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-oct-1-en-6-ynyl]-4-methyl-3,6-dihydro-2H-pyran 

Relevant academic research and scientific papers

Stereoselective synthesis of the C13-C28 subunit of (-)-laulimalide utilizing an α-chlorosulfide intermediate

A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An α-chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively. Georg Thieme Verlag Stuttgart, New York.

An improved synthesis of the C15-C28 fragment of laulimalide

The C15-C28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps from known epoxide 5, with an overall yield of 16%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-closing olefin metathesis chemistry. The 19,20-diol stereochemistry originates in starting material 7 and the side chain was appended using a Kocienski-modified Julia coupling.