94233-72-4

Upstream product

• 99493-25-1 diisopropyl (R,R)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 762-73-2 trimethyl(allyl)stannane 
• 99493-25-1 diisopropyl 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate (tartrate allylboronate) 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 762-72-1 allyl-trimethyl-silane 
• 1730-25-2 allylmagnesium bromide 
• 77287-11-7 methyl (S)-2-(benzyloxy)propanoate 
• 132836-85-2 (1R,5S,3Z)-1-acetoxy-5-benzyloxy-1-phenyl-3-hexene 
• 2551-83-9 allyltrimethoxysilane 
• 24850-33-7 allyltributylstanane 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 

Downstream Products

• 115043-57-7 ((2S,3S)-2-benzyloxy-hex-5-en-3-yloxy)(tert-butyl)dimethylsilane 
• 156327-31-0 (2S,3S)-2-benzyloxy-5-hexen-3-yl acetate 
• 94233-71-3 (4R,5S)-5-(phenylmethoxy)hex-1-en-4-ol 
• 1252651-79-8 C₁₉H₃₂O₂Si 
• 1339937-86-8 (4S,5S)-5-benzyloxy-4-methoxy-hexan-1-ol 
• 1339937-87-9 (4S,5S)-5-benzyloxy-4-O-acetyl-hexan-1-ol 
• 1339937-88-0 (4S,5S)-5-benzyloxy-4-methoxy-hexanal 
• 1339937-89-1 (4S,5S)-5-benzyloxy-4-O-acetyl-hexanal 
• 1318230-57-7 (-)-2-((2S,3S)-2-(benzyloxy)hex-5-en-3-yloxy)acetic acid 
• 1318230-86-2 syn,syn-(+)-(5R,6S)-5-((S)-1-(benzyloxy)ethyl)-6-vinyl-1,4-dioxan-2-one 
• 1318230-84-0 syn,anti-(-)-(5R,6R)-5-((S)-1-(benzyloxy)ethyl)-6-vinyl-1,4-dioxan-2-one 
• 1252651-80-1 C₁₉H₃₄O₃Si 
• 476212-27-8 {[(1S,2R)-2-(2-butynyloxy)-1-methyl-4-pentenyl]oxymethyl}benzene 
• 476212-29-0 {[(1S,2R)-1-methyl-2-(2-propynyloxy)-4-pentenyl]oxymethyl}benzene 

Relevant academic research and scientific papers

A Concise Synthesis of the Key Tetrahydrofuran Moieties of Caruifolin A and EBC-342

A common strategy for the concise synthesis of the key tetrahydrofuran moieties of caruifolin A and EBC-342 is presented. Asymmetric dihydroxylation and intramolecular SN2-cyclization are key strategic reactions for the synthesis of the furan f

Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction

A highly diastereoselective synthesis of trifluoromethylated 1,3-dioxanes is described. The reaction proceeds by an addition/oxa-Michael sequence and works efficiently under mild reaction conditions, with a good substrate scope and acceptable to good yiel

2,3,6-Trideoxy sugar nucleotides: Synthesis and stability

The synthesis and characterization of highly challenging 2,3,6-trideoxy sugar nucleotides were described for the first time. The study of their hydrolysis kinetics in aqueous buffers provided insight into their application as glycosyl donors.

Allylcopper intermediates with N-heterocyclic carbene ligands: Synthesis, structure, and catalysis

(Figure presented) Allylcopper Intermediates with N-heterocyclic carbene liganda are synthesized by transmetalation of allylsiloxane reagents, and the crystal structures of allylcopper compounds are reported. The allylcopper transmetalation is utilized fo

Glycosidation via conjugate addition of anomeric alkoxides to nitroalkenes and nitrosoalkenes

The conjugate addition reactions of protected pyranose alkoxides to both nitroalkenes and nitrosoalkenes, as a route to 2-nitroalkyl, 2-oximinoalkyl and 2-oxoalkyl glycosides, are described.

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.

Ligand effects in selective addition reactions of organoindium reagents with carbonyl compounds

The reaction of the allyl indium sesquibromide (CH2 =CHCH2)3In2Br3 with four equivalents of a bulky lithium alkoxide ((CH3)3COLi or (CH3)3CCH2OLi) results in modified reagents which show unusual degrees of chemo-and stereoselectivity in reactions with carbonyl compounds. For example, in reactions with cyclohexanone derivatives, 84-93% equatorial attack with preferential formation of the axial alcohols is observed. Chiral aldehydes react in a highly diastereoselective manner.

Preparation of Monosilyl Acetals from Esters via iBu2AlH Reduction and Trapping with N-(Trimethylsilyl)imidazole. Addition of Allyltrimethylsilane To Yield Homoallylic Alcohols or Ethers

Alkyl esters were reduced with iBu2AlH or a 1:1 mixture of iBu2AlH and iBu3Al (iBu2AlH*iBu3Al or iBu5Al2H), followed by trapping of the resulting tetrahedral intermediate with TMS-imidazole to produce monosilyl acetals.Reaction of the mixed acetals with allyltrimethylsilane in the presence of Lewis acids (Hosomi-Sakurai reaction) generated homoallylic alcohols or ethers selectively, depending on the substitution of the monosilyl acetal.TMS methoxy acetals (MeO-CH-OTMS) and TMS ethoxy acetals bearing additional complexing groups such as MeO- or Ph2C=N- provided alcohols with 1.5:1 - 9:1 threoselectivity, while simple TMS ethoxy acetals provided only ethyl ethers as products.The monosilyl acetal configuration was easily epimerized or racemized, and the configuration of the Hosomi-Sakurai product was apparently independent of the initial monosilyl acetal reactant configuration.

CHELATION CONTROLLED ALLYLATION OF ALDEHYDES WITH A CHIRAL ALLYLSILYLENE DERIVED FROM (-)-10-PHENYLPINANEDIOL

The chiral allylsilylene prepared from (-)-10-phenylpinanediol reacts with chiral α-alkoxy aldehydes in the presence of stannic chloride to afford homoallylic alcohols with diastereofacial selectivity ratios as high as 100:0.The results are consistent with attack of the allylsilylene on the less hindered face of the chelated intermediate.Our preliminary studies on several silylenes prepared from bicyclo systems revealed that substituent effects on the chiral auxiliary and the silicon atom play an important role in the selectivity of these unique compounds.

Effective 1,5-asymmetric induction in tin(IV) chloride promoted reactions between aldehydes and (4-alkoxy-2-alkenyl)tributylstannanes

Transmetallation of (S)-4-benzyloxy-2-pentenyl(tributyl)stannane (1) using tin(IV) chloride generates an allyltin trichloride which reacts in situ with aldehydes to give 1-substituted syn-(3Z)-5-benzyloxyhexenols with excellent stereoselectivity. With chiral aldehydes, the stereoselectivity of the reaction is dominated by the reagent, except for 2-alkoxyaldehydes which show matching and mismatching consistent with preferred Felkin-Anh diastereofacial selectivity.