127909-66-4

Upstream product

• 69152-87-0 4-benzyloxycrotonaldehyde 
• 80885-30-9 (E)-4-(benzyloxy)-2-buten-1-ol 
• 78469-85-9 (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol 
• 100-39-0 benzyl bromide 
• 87172-27-8 cis-4-benzyloxy-2,3-epoxy-1-butanol 
• 81028-03-7 (Z)-4-benzyloxy-but-2-en-1-ol 

Downstream Products

• 113123-34-5 (R)-1-((2S,3R)-3-Benzyloxymethyl-oxiranyl)-but-3-en-1-ol 
• 133285-30-0 (3S,4R,5R,6S)-7-benzyloxy-5,6-epoxy-3-(dimethylphenyl)silylhept-1-ene-4-ol 
• 133285-32-2 Acetic acid (E)-(R)-1-((2S,3S)-3-benzyloxymethyl-oxiranyl)-4-hydroxy-but-2-enyl ester 
• 142991-35-3 (2S,3R,4R)-5-Benzyloxy-4-chloro-pentane-2,3-diol 
• 142991-34-2 (2R,3R,4R)-1-Benzyloxy-3-bromo-pentane-2,4-diol 
• 113123-28-7 (S)-1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethanol 
• 113123-28-7 (R)-1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethanol 
• 133285-31-1 (E)-(4S,5S,6S)-7-benzyloxy-5,6-epoxy-hept-2-ene-1,4-diol 
• 133285-40-2 (3R,4R,5R,6S)-7-benzyloxy-5,6-epoxyhept-1-ene-3,4-diol 

Relevant academic research and scientific papers

Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates

The reaction of epoxy aldehydes with tetraethyl methylenediphosphonate gave γ,δ-epoxy vinyl phosphonates. The palladium-catalyzed addition of primary alcohols gave the monoprotected diols as single diastereoisomers. The trans- and cis-epoxides lead to opp

Stereocontrolled construction of tetrasubstituted tetrahydrofurans: Synthesis of 2,5-anhydro d-glucitol

A highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans has been accomplished by an unusual intramolecular 5-endo-tet cyclization of 2,3-epoxy alcohols involving hydroxyl nucleophile. The method has been utilized for the synthes

Asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes with hydrogen peroxide

The first asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes is presented. A chiral bisaryl-silyl-protected pyrrolidine acts as a very selective epoxidation organocatalyst using simple oxidation agents, such as hydrogen peroxide and tert-butyl hydroperoxide. The asymmetric epoxidation reactions proceed under environmental friendly reaction condition in, for example, water mixtures of alcohols, and the scope of the reaction is demonstrated by the formation of optically active α,β-epoxy aldehydes in high yields and enantioselectivities >94% ee. Furthermore, the direct synthesis of the sex pheromone from an acaric mite by asymmetric epoxidation of citral is presented. Copyright

Mukaiyama aldolisation reactions of α,β-epoxyaldehydes in aqueous media

The Mukaiyama aldolisation reaction in aqueous media of cis and trans α,β-epoxyaldehydes with tert-butyldimethylsilyl ketene acetal in the presence of Lewis's acids was studied. Sc(OTf)3 gave the best results in terms of selectivity. The same r

Palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols with double inversion of the configuration

A palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols is described, which proceeds with retention of the configuration, i.e., via two consecutive SN/s

A regio- and stereodivergent route to all isomers of vic-amino alcohols.

Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

A study on the chelation control in the regioselective opening of 2,3-bifunctionalized epoxides

The results obtained in the MgBr2-mediated opening of 2,3-bifunctionalized epoxides are reported. The studies showed that the chelation control of MgBr2 between different functionalities can in some cases be selective.

Aminolysis of vinyl epoxides as an efficient entry to N-H vinylaziridines

Vinyl epoxides 8a-f 11 and 12 have been prepared from the corresponding epoxy alcohols while 8g was formed by a regioselective epoxidation of the parent diene. Aminolysis of these materials resulted in a regio- and stereoselective nucleophilic opening at C3 in good yields except for the sterically hindered substrates. The trans-oxiranes gave the anti-amino alcohols while the cis derivative 12 gave the syn isomer 17. Cyclization of the anti-amino alcohols was best effected using the Mitsunobu protocol giving the corresponding N-H vinylaziridines in 50-54% yields, while the syn-amino alcohol 17 was transformed into the cis-vinylaziridine 31 with chlorosulfonic acid followed by base treatment in 20% yield. The outcome of these cyclizations seems to indicate that they are controlled by subtle steric effects in the substrate. The N-H vinylaziridine 24 was alkylated with tert-butyl bromoacetate and the product subjected to an aza[2,3]-Wittig rearrangement to give tetrahydropyridine 30 while acetylation of 24 followed by base treatment resulted in an aza-[3,3]-Claisen rearrangement yielding the seven-membered lactam 32.

HIGHLY REGIOSELECTIVE PALLADIUM-MEDIATED SUBSTITUTION OF ALLYLIC AND DIENYLIC CYCLIC CARBONATES

Reaction of chiral allylic and dienylic cyclic carbonates with various nucleophiles in the presence of (PPh3)4Pd as a catalyst afforded α-, γ-, or ε-substituted products with high regio-, (E)-stereo-, and diastereoselectivity depending on nucleophiles.

Reductive Cleavage Reaction of γ-Functionalized α,β-Unsaturated Esters and Halomethyls Mediated with Magnesium in Methanol

Reductive cleavage of various types of C-O and C-N bonds tethered to α,β-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of δ-hydroxy or δ-amino β,γ-unsaturated esters and allylic alcohols.Regardless of the geometry (E or Z) of the α,β-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters.The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.