cas 78342-42-4, (2S)-(+)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine

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78342-42-4

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An improved large scale synthesis of the Schoellkopf chiral auxiliaries: (2R)-and (2S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
Syntheses of the Schoellkopf chiral auxiliaries have been carried out on large scale in high overall yields from D- and L-valine. This method avoids the use of highly toxic phosgene or triphosgene, low-temperature reactions, and unstable intermediates.
Chen, Jianxie,Corbin, Scott P.,Holman, Nicholas J.
p. 185 - 187
(2012/12/24)

Practical synthesis of Schollkopf's bis-lactim ether chiral auxiliary: (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine
Practical methodology for the bis-O-methylation of (3S)-isopropyl-piperazine-2,5-dione 4 on a 45 g scale to generate Schollkopf's bis-lactim ether chiral auxiliary (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine 1 has been developed. Monomethylated intermediates 5 and 6 are reported for the first time. The gelling effects of 4 in a range of common solvents are also described.
Bull, Steven D.,Davies, Stephen G.,Moss, William O.
p. 321 - 327
(2007/10/03)

ENANTIOSELECTIVE SYNTHESIS OF NON-PROTEINOGENIC AMINO ACIDS VIA METALLATED BIS-LACTIM ETHERS OF 2,5-DIKETOPIPERAZINES
Bis-lactim ethers 1 of 2,5-diketopiperazines contain a chiral inducing center, an acidic CH-bond and two sites susceptible to hydrolysis.They react with BuLi to give Li compounds of type 4, 15, 29 or 32, which possess a prochiral C atom.They readily add electrophiles (such as alkylating agents or carbonyl compounds) with unusually high diastereoface differentiation.In many cases the d.e-value (d.e. = diastereomeric excess = asymmetric induction) of the adduct exceeds 95percent.On hydrolysis the adducts are cleaved liberating the chiral auxiliary (used to build up the bis-lactim ether 1) and the target molecules, the optically active amino acid methyl esters of type 8, 19, 25 or 36.The two amino acid esters are separable either by fractional distillation or (eventually after further hydrolysis to amino acids) by chromatography.Transition state models are discussed that could explain the exceptionally high asymmetric induction and the predictability of the induced configuration.
Schoellkopf, Ulrich
p. 2085 - 2092
(2007/10/02)

Enantioselektive Synthese von (R)-Aminosaeuren unter Verwendung von L-Valin als chiralen Hilfsstoff
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Schoellkopf, Ulrich,Groth, Ulrich,Deng, Chuanzheng
p. 793 - 795
(2007/10/02)

Chemical Properties

Appearance/Colour :Clear colorless to pale yellow liquid
Boiling Point: 245.2 °C at 760 mmHg
Flash Point:85.6 °C
Density: 1.09 g/cm³
Solubility:Chloroform (Slightly), DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly)
Storage Temp.:Store below +30°C.
Vapor Pressure: 0.0456mmHg at 25°C
Refractive Index: 1.503
PKA: 3.81±0.60(Predicted)
BRN: 3650245
PSA: 43.18000
LogP: -0.01440

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Chemical Properties

Appearance/Colour :Clear colorless to pale yellow liquid

Boiling Point: 245.2 °C at 760 mmHg

Flash Point:85.6 °C

Density: 1.09 g/cm³

Solubility:Chloroform (Slightly), DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly)

Storage Temp.:Store below +30°C.

Vapor Pressure: 0.0456mmHg at 25°C

Refractive Index: 1.503

PKA: 3.81±0.60(Predicted)

BRN: 3650245

PSA: 43.18000

LogP: -0.01440

Global suppliers and manufacturers of 78342-42-4total 55 suppliers on LookChem

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78342-42-4

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Chemical Properties

Appearance/Colour :Clear colorless to pale yellow liquid

Boiling Point: 245.2 °C at 760 mmHg

Flash Point:85.6 °C

Density: 1.09 g/cm3

Solubility:Chloroform (Slightly), DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly)

Storage Temp.:Store below +30°C.

Vapor Pressure: 0.0456mmHg at 25°C

Refractive Index: 1.503

PKA: 3.81±0.60(Predicted)

BRN: 3650245

PSA: 43.18000

LogP: -0.01440

Global suppliers and manufacturers of 78342-42-4total 55 suppliers on LookChem

Density: 1.09 g/cm³