175431-85-3

Usage

InChI:InChI=1/C5H11NO/c1-2-5(6)3-4-7/h2,5,7H,1,3-4,6H2

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 440366-54-1 2-(carbobenzyloxy)amino-4-butyrolactol 
• 31332-88-4 (S)-3-(N-benzyloxycarbonylamino)tetrahydrofuran-2-one 
• 913337-74-3 {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-allyl}-carbamic acid tert-butyl ester 

Downstream Products

• 916677-46-8 N-[1-(2-hydroxyethyl)allyl]-4-methylphenylsulfonylamide 
• 175431-36-4 3-(N-benzoylamino)pent-4-en-1-ol 
• 175431-34-2 3-(Ethoxycarbonylamino)-4-penten-1-ol 

Relevant academic research and scientific papers

Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine

A new enantioselective catalysis has been developed for the one-step construction of methylene-bridged chiral modules of 1,2- and 1,3-OH and/or NH function(s) from δ- or λ-OH/NHBoc-substituted allylic alcohols and H2C=O / H2C=NBoc . A protonic nucleophile, either in situ-generated CH2OH or CH2NHBoc, is intramolecularly allylated to furnish eight possible 1,2- or 1,3-O,O, -O,N, -N,O, and -N,N chiral modules equipped with an ethenyl group in high yields and enantioselectivities. The utility of this method has been demonstrated in the five-step synthesis of sphingosine.

Pseudosymmetry in azabicyclo[2.1.1]hexanes. A stereoselective construction of the bicyclic core of peduncularine

Intramolecular photocycloaddition of 41 or its equivalent leads to the formation of photoadduct 25. While retro-Mannich fragmentation of the "b" bond in 25 leads to the formation of 44 (via 43), with the incorrect relative stereochemistry for the synthesi

Novel synthesis of [1-11C]γ-vinyl-γ-aminobutyric acid ([1-11C]GVG) for pharmacokinetic studies of addiction treatment

γ-Vinyl-γ-aminobutyric acid (GVG, Vigabatrin), a suicide inhibitor of GABA-transaminase (GABA-T), has been suggested as a new drug for the treatment of substance abuse. In order to better understand its pharmacokinetics and potential side effects, we have developed a radiosynthesis of carbon-11 (t1/2=20min) labeled GVG for positron emission tomographic (PET) studies. We report here a novel synthetic strategy to prepare the precursor and to efficiently label GVG with C-11. 5-Bromo-3-(carbobenzyloxy)amino-1-pentene was synthesized in five steps from homoserine lactone, including reduction and methylenation. This was used in a one-pot, two-step radiosynthesis. Displacement of bromide with no-carrier-added [11C]cyanide followed by acid hydrolysis afforded [1-11C]GVG with decay corrected radiochemical yields of 27 ± 9% (n=6, not optimized) with respect to [11C]cyanide in a synthesis time of 45 min. Copyright

Pronounced electronic effect of allylic amino groups on the π-facial stereoselectivity and reactivity of the iodoetherification of N-substituted 3-amino-4-penten-1-ols

The iodoetherification of N-substituted 3-amino-4-penten-1-ol (1) [I2 and NaHCO3 (2 equivalents each) in ether/H2O at 0°C], providing the mixtures of N-substituted cis- and trans-3-amino-2-iodomethyltetrahydrofurans (9), d