143360-25-2

Upstream product

• 81028-12-8 (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 
• 106-96-7 propargyl bromide 
• 40963-57-3 2-Propynylzinc bromide 
• 3673-14-1 2,3:4,5-di-D-isopropylidene-D-xylose diethyl dithioacetal 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 19139-73-2 (4R,4'R,5S)-5-((benzyloxy)methyl)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolane) 
• 30737-85-0 2,3,4,5-di-O-isopropylidene-D-xylitol 
• 13039-94-6 2,3,4,5-di-O-isopropylidene-D-xylose aldehyde 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 78469-77-9 (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 143360-26-3 [(S)-1-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-ynyloxy]-tert-butyl-dimethyl-silane 
• 476212-36-9 (4R,5R)-4-[(1R)-1-(allyloxy)-3-butynyl]-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 
• 496920-50-4 4-benzyloxymethyl-2,2-dimethyl-5-(4-vinyl-2,3-dihydrofuran-2-yl)[1,3]dioxolane 
• 496920-85-5 6,8-dioxo-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-2H-1-oxa-7-aza-as-indacene-2-carbaldehyde 
• 496920-60-6 2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-2,3,5,5a,8a,8b-hexahydro-1-oxa-7-aza-as-indacene-6,8-dione 
• 496920-62-8 2-(5-benzyloxymethyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)-7-phenyl-2,3,5,5a,8a,8b-hexahydro-1-oxa-7-aza-as-indacene-6,8-dione 
• 143360-28-5 [(Z)-(S)-1-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-3-enyloxy]-tert-butyl-dimethyl-silane 
• 143360-27-4 [(S)-1-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-3-ynyloxy]-tert-butyl-dimethyl-silane 
• 66018-41-5 zeaenol 

Relevant academic research and scientific papers

Convergent and stereoselective synthesis of (-)-zeaenol

Stereoselective synthesis of (-)-zeaenol has been accomplished from d-xylose as a chiral pool starting material. The key steps of this convergent synthetic strategy involves a Stille coupling, a Noyori reduction, a Julia-Kocienski olefination and a macrolactonization to obtain (-)-zeaenol. We have also explored a Sonogashira coupling along with a Trost protocol for the intramolecular hydrosilylation on the homopropargylic alcohol system as an alternative synthetic approach to this molecule.

A facile synthesis of enantiopure tricyclic furanyl and pyranyl derivatives via tungsten-mediated cycloalkenation and Diels-Alder reaction

We report the synthesis of chiral furanyl and pyranyl dienes 1 and 2 based on cycloalkenation of chiral tungsten alkynol complexes. These two dienes bear a chiral 1,3-dioxolane group to control diastereoselective Diels-Alder reactions with electron-deficient olefins. The chiral 1,3-dioxolane substituents of the cycloadducts were degraded into hydrogen atoms to make these molecules possess common furan and pyran rings. Dienes 1 and 2 are good building blocks for enantiopure forms of tricyclic oxygen compounds.

Synthesis of chiral oxacyclic dienes via ruthenium-catalyzed enyne metathesis: Useful building blocks for chiral tricyclic oxygen derivatives

Various chiral oxacyclic dienes were synthesized via enyne metathesis using Grubbs catalyst (PCy3)2Cl2Ru=CHPh. A series of substrates bearing a 1,2-diol skeleton was prepared from (2S)-(benzyloxy)-propanal. The enyne metathesis proceeds smoothly in CH2Cl2 at 23°C with a low loading of catalyst (2.0mol%) under ethylene gas (1-2.5atm), giving good yields of products without epimerization at any stereogenic carbon. Heating compound 5 comprising a disubstituted alkyne in benzene (80°C) under nitrogen resulted in formation of two diastereomers via epimerization of the primary product. The epimerization occurs at the oxacyclic carbon rather than the benzyl carbon. Diels-Alder reactions of chiral oxacyclic dienes 19 and 22 with maleic anhydride, maleimide and benzoquinone proceeded with high diastereoselectivities, yielding a single cycloadduct efficiently at ambient conditions. The structures of Diels-Alder adducts were determined by 1H NOE NMR spectra. The cycloadducts were formed via the approach of dienophiles to the diene in endo mode and opposite the substituent of the stereogenic center. The cycloadducts 29 and 31 were transformed into enantiopure tricyclic furans 35 and 38 after transformation of the (2S)-(silyloxy)ethyl group into an acetate group.

Facile synthesis of enantiopure tricyclic furanyl derivatives via tungsten-mediated cycloalkenation reactions and Diels-Alder reactions

Chiral furanyl diene 1 is easily prepared from cycloalkenation of chiral tungsten alkynol with acetaldehyde, followed by demetalation with Me3NO. This diene bears a chiral 1,3-dioxolane group to control diastereoselective Diels-Alder reactions

Stereoselective Syntheses of Two Constituents Against Rice Blast Disease

(11S,12S,13S)-Trihydroxy-(9Z,15Z)-octadecanoic acid 1 and methyl (11R,12S,13S)-11-hydroxy-12,13-epoxyoctadecadienoate 3a were synthesized starting from L-(+)- and D-(-)-tartaric acids, respectively.