3588-63-4

Basic information

• Product Name: N-CARBOBENZOXY-DL-VALINE
• Synonyms: Z-DL-VALINE extrapure;(±)-N-[(Phenylmethoxy)carbonyl]valine;N-[(Phenylmethoxy)carbonyl]-DL-valine;2-(benzyloxycarbonylamino)-3-methyl-butyric acid;N-Cbz-DL-valine Z-DL-Val-OH;Z-DL-Val;Cbz-DL-valine;DL-Cbz valine
• CAS NO: 3588-63-4
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.28
• EINECS: 222-727-4
• Product Categories: Cbz-Amino Acids;Amino Acids;Amino Acids (N-Protected);Biochemistry
• Mol File: 3588-63-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 78 °C
• Boiling Point: 432.6 °C at 760 mmHg
• Flash Point: 215.4 °C
• Appearance: Off-white to white/Powder
• Density: 1.182 g/cm³
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Methanol
• CAS DataBase Reference: N-CARBOBENZOXY-DL-VALINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZOXY-DL-VALINE(3588-63-4)
• EPA Substance Registry System: N-CARBOBENZOXY-DL-VALINE(3588-63-4)

Safety Data

• Statements: 52/53
• Safety Statements: 61-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3588-63-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C13H17NO4/c1-9(2)11(12(15)16)14-13(17)18-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3,(H,14,17)(H,15,16)

Upstream product

• 516-06-3 D,L-valine 
• 91806-74-5 3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester 
• 100-51-6 benzyl alcohol 
• 501-53-1 benzyl chloroformate 
• 20314-88-9 tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate 

Downstream Products

• 134306-34-6 N-(Benzyloxycarbonyl)valine methyl ester 
• 879123-73-6 N-(N-benzyloxycarbonyl-valyl)-alanine ethyl ester 
• 20803-40-1 N-(N-benzyloxycarbonyl-valyl)-glycine methyl ester 
• 76444-98-9 valine cyclohexyl ester 
• 56414-85-8 N-benzyloxycarbonyl-valine thiazol-2-ylamide 
• 18054-21-2 N-Carbobenzoxy-DL-valin-trimethylsilylester 
• 15054-16-7 N-Carbobenzoxy-DL-valin-N-2-chloroethylamid 
• 119071-05-5 Z-L-Val-L-Hyp(tBu)-OtBu 
• 101865-15-0 2-Benzyloxycarbonylamino-3-methyl-butyric acid cyclopentyl ester 
• 219323-47-4 Z-D-Val-NH-(CH₂)3CH₃ 
• 32402-31-6 N-benzyloxycarbonyl-(2R)-valinylglycine methyl ester 
• 876624-35-0 {2-methyl-1-[4-(1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-thiazolidine-3-carbonyl]-propyl}-carbamic acid benzyl ester 
• 1429788-33-9 N-(N-(benzyloxycarbonyl)-DL-valyl)-3-(trimethylstannyl)alanine methyl ester 
• 1429788-34-0 N-(N-(benzyloxycarbonyl)-DL-valyl)-3-(trimethylstannyl)alanine ethyl ester 

Relevant articles and documents

Chiral tetraaryl-and tetraalkynylborates as chiral solvating agents for tetraalkylammonium salts

The application of tetracarbon-substituted chiral borate sodium salts (NaBR*4) as NMR chiral solvating agents for various tetraalkylammonium salts (R4NX) has been successfully demonstrated. Ion exchange between R4NX and NaBR*4 proceeded in excellent yields and provided the corresponding dia-stereomeric salts (R4NBR*4). The ee values of the R4NX salts were determined by1H NMR analysis of R4NBR*4. Two types of chiral borates, tetraaryl-and tetraalkynylborates with optically active 1,1′-binaphthyl components were used. At the beginning of this research, we investigated the efficacy of a known chiral tetraar-ylborate developed by Pommerening et al. for R4NX. To expand the possibility of further structural design of the chiral borate, we designed chiral tetraalkynylborates as a new structure. Their synthesis and application are also described.

Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor

(Chemical Equation Presented) A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-α-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.

A novel concept in combinatorial chemistry in solution with the advantages of solid-phase synthesis: Formation of N-betaines by multicomponent domino reactions

Advantages of solid-phase and liquid-phase synthesis are combined in a new concept of combinatorial chemistry: a domino sequence comprising Knoevenagel and hetero-Diels-Alder reactions, with subsequent hydrogenation starting from protected aminoaldehydes, 1.3-dicarbonyl compounds, and enol ethers leads to N-heterocycles of high diversity with a betaine structure, which are isolated in highly pure form by precipitation with diethyl ether (see scheme), Cbz = benzylocycarbonyl, Bn = benzyl.