84907-75-5

Basic information

• Product Name: (2R,5S)-2,5-dihydro-5-isopropyl-3,6-dimethoxy-2-methyl-2-(1'-phenylethenyl)-pyrazine
• CAS NO: 84907-75-5
• Molecular Weight: 300.401
• Mol File: 84907-75-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,5S)-2,5-dihydro-5-isopropyl-3,6-dimethoxy-2-methyl-2-(1'-phenylethenyl)-pyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-2,5-dihydro-5-isopropyl-3,6-dimethoxy-2-methyl-2-(1'-phenylethenyl)-pyrazine(84907-75-5)
• EPA Substance Registry System: (2R,5S)-2,5-dihydro-5-isopropyl-3,6-dimethoxy-2-methyl-2-(1'-phenylethenyl)-pyrazine(84907-75-5)

Safety Data

• Hazardous Substances Data: 84907-75-5(Hazardous Substances Data)

Upstream product

• 914399-92-1 (6S)-6-isopropyl-5-methoxy-3-methyl-3,6-dihydro-2-pyrazinyl methyl ether 
• 98-86-2 acetophenone 
• 24601-74-9 (S)-4-isopropyloxazolidine-2,5-dione 
• 15136-26-2 cyclo(L-Val-D,L-Ala) 
• 28140-49-0 L-Val-D,L-Ala-OCH₃ 
• 72-18-4 L-valine 
• 98-88-4 benzoyl chloride 
• 115228-42-7 (2S,5S)-2-benzoyl-2,5-dihydro-5-isopropyl-3,6-dimethoxy-2-methylpyrazine 
• 19493-09-5 Methylenetriphenylphosphorane 
• 84907-70-0 1-((2R,5S)-5-Isopropyl-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazin-2-yl)-1-phenyl-ethanol 

Downstream Products

• 84907-73-3 (R)-α-(1-phenylethenyl)alanine methyl ester 
• 4070-48-8 L-Valine methyl ester 

Relevant articles and documents

Asymmetric Syntheses via Heterocyclic Intermediates, XL. - Studies on the Acylation of Lithiated Bislactim Ethers of cyclo(-L-Val-Ala-) and cyclo(-L-Val-Gly-). - Asymmetric Synthesis of (R)-α-Alkenyl and (R)-α-Ethinyl Alanine Methyl Esters by the Bislactim Ether Method

The lithiated bislactim ether 2a of cyclo(-L-Val-Ala-) reacts with acyl chlorides 3 highly diastereoselectively to yield the compounds 4 with (2S,5S)-configuration.With acetyl chloride (3a) the N-acetyl compound 7 is formed as a sideproduct.Alternatively, the compounds 4 can be obtained by oxidation of the carbinols 8.From 4a and b, the olefins 11a and b are obtained by Wittig reaction.These are precursors of methyl (R)-α-alkenyl alanine methyl esters of type 13. (R)-α-ethinyl alanine methyl ester 17 is obtainable from 4a and 4e via the intermediates 14 or 15 and16a.The lithiated bislactim ether 2c of cyclo(-L-Val-Gly-) reacts with benzoyl chloride (3b) to give the "bis adduct" 18.However, 6b is obtained from 2c and the benzamide 19, though as a 1:1 diastereomeric mixture.Presumably, 6b epimerizes via the enol 21a subsequently to its diastereoselective formation.

Asymmetric Syntheses via Heterocyclic Intermediates; XIII. Enantioselective Synthesis of (R)-α-Alkenylalanine Methyl Esters using L-Valine as Chiral Auxiliary Reagent

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