958635-16-0

Upstream product

• 103791-54-4 (+/-)-6-[(tert-butyldiphenylsilyl)oxy]-1,2-epoxyhexane 
• 185999-07-9 tert-butyl(hex-5-enyloxy)diphenylsilane 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 958635-26-2 (R)-6-[(tert-butyldiphenylsilyl)oxy]hexane-1,2-diol 
• 821-41-0 5-Hexen-1-ol 

Downstream Products

• 1207434-34-1 (R)-8-(tert-butyldiphenylsilyloxy)-1-(trimethylsilyl)oct-1-yn-4-ol 
• 1207434-35-2 (R)-8-(tert-butyldiphenylsilyloxy)oct-1-yn-4-ol 
• 1207434-17-0 (R)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-5-(prop-2-ynyl)-4,10-dioxa-3,11-disilatridecane 
• 1207434-22-7 (5S,6S,9R,11R,E)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,9,18,18-octamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-7-ene 
• 1207434-21-6 (5S,6S,7R,11R,Z)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-en-7-ol 
• 1207434-19-2 (5S,6R,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-one 
• 1207434-38-5 (5S,6S,7R,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol 
• 1207434-20-5 (5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol 
• 1434059-28-5 (R)-7-(tert-butyldiphenylsilyloxy)hept-1-en-3-ol 
• 1434059-29-6 (R)-tert-butyl(5-(4-methoxybenzyloxy)hept-6-enyloxy)diphenylsilane 
• 1434059-30-9 (R)-5-(4-methoxybenzyloxy)hept-6-en-1-ol 
• 1434059-31-0 (R)-5-(4-methoxybenzyloxy)hept-6-enal 
• 1206732-10-6 (2S,5R)-5-[(4-methoxybenzyl)oxy]hept-6-ene-1,2-diol 
• 1434059-32-1 (S)-2-((R)-3-(4-methoxybenzyloxy)pent-4-enyl)oxirane 

Relevant academic research and scientific papers

Total synthesis and revision of the absolute configuration of seimatopolide B

The asymmetric total synthesis of natural seimatopolide B along with its enantiomer is described starting from readily available 5-hexen-1-ol and 3-buten-1-ol. The key steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxyl

Study of the total synthesis of (-)-exiguolide

In this article, we disclose the various routes and strategies we had to explore before finally achieving the total synthesis of (-)-exiguolide ((-)-1). Two first types of approaches were set, both relying on the Trost's domino ene-yne coupling/oxa-Michael reaction that we choose for its ability to control the geometry of the methylacrylate-bearing tetrahydropyrane ring B. In our first approach, we expected to assemble the two main fragments (C14-C21 and C1-C13) by creating the C13-C14 bond through a palladium(0)-catalyzed cross-coupling, but this step failed, unfortunately. In the second approach, which was more linear, we created the C16-C17 bond through condensation of a lithium acetylide on a Weinreb amide, and we assembled the C1-C5 and C6-C21 subunits through Trost's domino ene-yne coupling/oxa-Michael reaction. These two approaches served us to design an ameliorated third strategy, which finally led to the total synthesis of (-)-exiguolide.

Total synthesis of (-)-exiguolide

The first total synthesis of the naturally occurring enantiomer of exiguolide ((-)-1) has been completed. This very convergent synthesis features the following as main steps: (I) a Trost's ruthenium-catalyzed ene-yne cross-coupling reaction (this complex transformation allows the challenging control of the C5-C28 double bond geometry along with the stereoselective construction of the tetrahydropyran ring A) and (II) a very efficient one-pot, two-step stereoselective conjugated allyllc alcohol substitution that allowed the control of the C15 stereogenic center.

"Cassette" in situ enzymatic screening identifies complementary chiral scaffolds for hydrolytic kinetic resolution across a range of epoxides

(Figure Presented) Put the cassette in: An in situ enzymatic screen can give real-time estimates of the sense and magnitude of enantioselectivity across more than one substrate. Screening identified CoIII-salen catalysts with β-pinene- and α-naphthylalanine-derived chiral scaffolds with broad, yet complementary, substrate specificities. ADH = alcohol dehydrogenase, HL = horse liver, LK = Lactobacillus kefir, salen = (salicylidene) ethylenediamine.