84573-21-7

Basic information

• Product Name: (±)-3-((benzyloxy)methyl)oxirane-2-carbaldehyde
• CAS NO: 84573-21-7
• Molecular Weight: 192.214
• Mol File: 84573-21-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (±)-3-((benzyloxy)methyl)oxirane-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-3-((benzyloxy)methyl)oxirane-2-carbaldehyde(84573-21-7)
• EPA Substance Registry System: (±)-3-((benzyloxy)methyl)oxirane-2-carbaldehyde(84573-21-7)

Safety Data

• Hazardous Substances Data: 84573-21-7(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 81028-03-7 (Z)-4-benzyloxy-but-2-en-1-ol 
• 87172-27-8 cis-4-benzyloxy-2,3-epoxy-1-butanol 

Downstream Products

• 113123-28-7 (S)-1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethanol 
• 113123-28-7 (R)-1-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethanol 
• 142991-34-2 (2R,3R,4R)-1-Benzyloxy-3-bromo-pentane-2,4-diol 
• 142991-35-3 (2S,3R,4R)-5-Benzyloxy-4-chloro-pentane-2,3-diol 
• 113123-34-5 (R)-1-((2S,3R)-3-Benzyloxymethyl-oxiranyl)-but-3-en-1-ol 
• 188896-08-4 2-(benzyloxy)-1-cyclopropyl-1-ethanol 
• 14869-02-4 1-Benzyloxy-penten-⁽³⁾-ol-⁽²⁾ 

Relevant articles and documents

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

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.