15136-27-3

Basic information

• Product Name: CYCLO(-D-ALA-VAL)
• Synonyms: CYCLO(-D-ALA-VAL)
• CAS NO: 15136-27-3
• Molecular Formula: C₈H₁₄N₂O₂
• Molecular Weight: 170.21
• Mol File: 15136-27-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 429.7±38.0 °C(Predicted)
• Appearance: /
• Density: 1.040±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 13.16±0.60(Predicted)
• CAS DataBase Reference: CYCLO(-D-ALA-VAL)(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLO(-D-ALA-VAL)(15136-27-3)
• EPA Substance Registry System: CYCLO(-D-ALA-VAL)(15136-27-3)

Safety Data

• Hazardous Substances Data: 15136-27-3(Hazardous Substances Data)

Upstream product

• 72-18-4 L-valine 
• 14316-06-4 D-alanine methyl ester hydrochloride 
• 24601-74-9 (S)-4-isopropyloxazolidine-2,5-dione 
• 13734-41-3 t-Boc-L-valine 
• 16944-60-8 (2S)-isopropylpiperazine-3,6-dione 
• 205517-35-7 (3S,6R)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-methyl-piperazine-2,5-dione 
• 77935-28-5 Boc-Val-D-Ala-OBzl 
• 28140-49-0 L-Val-D,L-Ala-OCH₃ 
• 205517-34-6 (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione 

Downstream Products

• 81136-86-9 (3S,6S,R)-2,5-Dimethoxy-3-isopropyl-6-methyl-3,6-dihydropyrazine 
• 338-69-2 D-Alanine 
• 72-18-4 L-valine 
• 205517-35-7 (3S,6R)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-methyl-piperazine-2,5-dione 
• 81136-88-1 (2R,5S)-2-(3,4-Dimethoxy-benzyl)-5-isopropyl-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine 
• 81136-89-2 (2R,5S)-5-Isopropyl-3,6-dimethoxy-2-methyl-2-((E)-3-phenyl-allyl)-2,5-dihydro-pyrazine 
• 81136-87-0 (2S,5R)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-benzyl-5-methylpyrazine 
• 84907-70-0 1-((2R,5S)-5-Isopropyl-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazin-2-yl)-1-phenyl-ethanol 
• 83537-81-9 (3R,6S)-3-[(benzyloxy)methyl]-6-isopropyl-1,4-dimethoxy-3-methyl-3,6-dihydropyrazine 
• 88050-50-4 (3R,6S)-3-(2-benzylthioethyl)-6-isopropyl-2,5-dimethoxy-3-methyl-3,6-dihydropyrazine 
• 84907-75-5 (2R,5S)-2,5-dihydro-5-isopropyl-3,6-dimethoxy-2-methyl-2-(1'-phenylethenyl)-pyrazine 

Relevant articles and documents

A chiral relay auxiliary for the synthesis of homochiral α-amino acids

A new chiral auxiliary (3S)-N,N′-bis(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione 7 has been developed for the asymmetric synthesis of α-amino acids. The auxiliary 7 employs a novel chiral relay network based on non-stereogenic N-benzyl protecting groups which enhance the diastereoselectivity observed during alkylation of its C6 enolate 25.

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.

Asymmetric syntheses via heterocyclic intermediates; VIII. Enantioselective synthesis of (R)-α-methyl-α-amino acids using L-valine as chiral auxiliary reagent

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