79069-50-4

Basic information

• Product Name: Boc-L-alaninal
• Synonyms: BOC-L-ALANINAL;BOC-L-ALANINE ALDEHYDE;BOC-ALANINE-ALDEHYDE;BOC-ALA-ALDEHYDE;N-T-BOC-L-ALANINE ALDEHYDE;N-T-BOC-L-ALANINAL;Carbamic acid, [(1S)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI);(S)-t-butyl 1-oxopropan-2-yl carbamate
• CAS NO: 79069-50-4
• Molecular Formula: C₈H₁₅NO₃
• Molecular Weight: 173.21
• Product Categories: N-BOC;A - H;Aldehydes;Amino Acids;B;Bioactive Small Molecules;Biochemicals and Reagents;Building Blocks;C8;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Modified Amino Acids;Organic Building Blocks
• Mol File: 79069-50-4.mol

Chemical Properties

• Melting Point: 76-77 °C
• Boiling Point: 248.5 °C at 760 mmHg
• Flash Point: 104.1 °C
• Appearance: White to yellow/Powder
• Density: 1.015 g/cm³
• Vapor Pressure: 0.0241mmHg at 25°C
• Refractive Index: 1.435
• Storage Temp.: −20°C
• Solubility: soluble in Methanol
• PKA: 11.43±0.46(Predicted)
• CAS DataBase Reference: Boc-L-alaninal(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-alaninal(79069-50-4)
• EPA Substance Registry System: Boc-L-alaninal(79069-50-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 79069-50-4(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow powder

InChI:InChI=1/C8H15NO3/c1-6(5-10)9-7(11)12-8(2,3)4/h5-6H,1-4H3,(H,9,11)/t6-/m0/s1

Upstream product

• 79069-13-9 (S)-2-t-butoxycarbonylaminopropan-1-ol 
• 209113-02-0 N-Boc-(S)-alanine-pivalic acid mixed anhydride 

Downstream Products

• 130832-55-2 [(1S,2S)-2-(4-Chloro-2-hydroxy-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 115378-33-1 (-)-tert-butyl [(1S)-1-methylprop-2-en-1-yl]carbamate 
• 130832-53-0 [(1S,2S)-2-(4-tert-Butyl-2-hydroxy-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 130832-54-1 [(1S,2R)-2-(4-tert-Butyl-2-hydroxy-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 104739-58-4 N-(2-Boc-aminopropyliden)-L-phenylalanin-N-oxid-methylester 
• 123172-83-8 [(1S,2R)-2-Hydroxy-2-(2-hydroxy-5-methoxy-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 123172-82-7 (S,1'S)-2-hydroxy-5-methoxy-α-<1'-Boc-2'-aminoethyl>benzenemethanol 
• 873009-27-9 (R)-tert-butyl 4,4-dibromobut-3-en-2-ylcarbamate 
• 176962-17-7 ((S)-3,3-Dibromo-1-methyl-allyl)-carbamic acid tert-butyl ester 
• 1034089-14-9 (2S,3SR)-2-{[(tert-butoxy)carbonyl]amino}hex-5-en-3-ol 
• 142723-69-1 [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-pentenoic acid 

Relevant articles and documents

Synthesis and Characterization of Optically Pure Gamma-PNA Backbones by SIBX-Mediated Reductive Amination

Chiral peptide nucleic acid (PNA) is a derivative of regular PNA by introducing a chiral center to its backbone, and is known to bind more strongly to DNA or RNA than regular PNA. In particular, in the case of a γ-backbone, the L isomer stabilizes the PNA/DNA duplex, and the D-isomer has the opposite effect. Therefore, the synthesis of an optically pure γ-backbone is very important. Here, we report a novel synthetic strategy for the suppression of epimerization during the synthesis of the γ-PNA backbone. A stabilized form of 2-iodoxybenzoic acid (SIBX) was used as an oxidative reagent in the key intermediate of the N-Boc-amino acetaldehyde synthesis. This paper reports (1) the synthesis and comparison of three different γ-PNA backbones (lysine, alanine, and glutamate) by three different synthetic routes (SIBX, lithium aluminum hydride, and Red-Al) and (2) the determination of chiral purity from their derivative compounds. The enantiomeric excess purity of SIBX-mediated γ-PNA backbones was determined to be more than 99.4%, as ascertained by the high-performance liquid chromatography (HPLC) chromatogram on a standard RP-C18 column. It is comparatively higher than that of the other methods examined in this work.

Synthetic Studies on the Preparation of Alanyl Epoxysulfones as Cathepsin Cysteine Protease Electrophilic Traps

A Darzens reaction between tert-butoxycarbonyl alaninal and chloromethyl phenyl sulfone afforded chlorohydrins, which were converted into epoxysulfones by reaction with sodium tert-butoxide. Epoxysulfone 10 and chloroketone 14 derived from chlorohydrins by oxidation proved to be inhibitors of cathepsins H, S, and C as determined by competitive activity-based protein profiling.

A direct and efficient stereoconservative procedure for the selective oxidation of N-protected β-amino alcohols

An efficient, very simple and eco-friendly procedure has been developed for the synthesis of highly enantioenriched α-amino aldehydes by IBX-mediated oxidation of the corresponding β-amino alcohols. The procedure has been applied to a wide range of substr

An easy and fast conversion of N2-[(tert-butoxy)carbonyl]-L-amino acids to corresponding amino-aldehydes

A new method for the preparation of N2-[(tert-butoxy)carbonyl]-L-amino-aldehydes from N2-[(tert-butoxy)carbonyl]-L-amino acids based on reduction of mixed anhydrides with LiAl(t-BuO)3H is described.