108957-20-6

Basic information

• Product Name: N-BOC-3-IODO-L-ALANINE BENZYL ESTER
• Synonyms: BOC-3-IODO-L-ALANINE BENZYL ESTER;N-BOC-3-IODO-L-ALANINE BENZYL ESTER;N-(TERT-BUTOXYCARBONYL)-3-IODO-L-ALANINE BENZYL ESTER;(R)-2-TERT-BUTOXYCARBONYLAMINO-3-IODO-PROPIONIC ACID BENZYL ESTER;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-IODO-PROPIONIC ACID BENZYL ESTER;Boc-beta-iodo-Ala-OBzl;boc-β-iodo-ala-obzl;BOC-3-IODO-ALA-OBZL
• CAS NO: 108957-20-6
• Molecular Formula: C₁₅H₂₀INO₄
• Molecular Weight: 405.23
• EINECS: 200-258-5
• Mol File: 108957-20-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 78-80 °C(lit.)
• Boiling Point: 460.1 °C at 760 mmHg
• Flash Point: 232 °C
• Appearance: /
• Density: 1.485 g/cm³
• Vapor Pressure: 1.2E-08mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: 2-8°C
• PKA: 10.42±0.46(Predicted)
• Sensitive: Light Sensitive
• BRN: 4506658
• CAS DataBase Reference: N-BOC-3-IODO-L-ALANINE BENZYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-3-IODO-L-ALANINE BENZYL ESTER(108957-20-6)
• EPA Substance Registry System: N-BOC-3-IODO-L-ALANINE BENZYL ESTER(108957-20-6)

Safety Data

• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 108957-20-6(Hazardous Substances Data)

Usage

Uses

N-Boc-3-iodo-L-alanine Benzyl Ester is used as a reactant in the synthesis of the angiotensin-converting enzyme Inhibitors (-)-A58365A and (-)-A58365B lactams.

InChI:InChI=1/C15H20INO4/c1-15(2,3)21-14(19)17-12(9-16)13(18)20-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,19)/t12-/m0/s1

Upstream product

• 94882-74-3 benzyl 2(S)-(tert-butoxycarbonylamino)-3-p-toluenesulfonylpropionate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3695-68-9 L-serine benzyl ester benzenesulfonate salt 
• 100-51-6 benzyl alcohol 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 100-39-0 benzyl bromide 
• 59524-02-6 N-tert-butoxycarbonyl-L-serine benzyl ester 

Downstream Products

• 127977-27-9 benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(2'-pyridyl)propionate 
• 125942-82-7 benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4-oxo-4-(2'-furyl)butanoate 
• 149775-92-8 benzyl (2S,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-isopropylidenedioxy-4-oxohexanoate 
• 149775-93-9 benzyl (2R,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-isopropylidenedioxy-4-oxohexanoate 
• 141362-39-2 Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4(R/S)-(bromomethyl)hex-5-enoate 
• 127977-23-5 benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(4'-fluorophenyl)propionate 
• 127977-21-3 benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(4'-acetoxyphenyl)propionate 
• 141362-44-9 Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-5-methylhex-5-enoate 
• 141527-81-3 benzyl 2(S)-<(tert-butoxycarbonyl)amino>-4-oxo-6-phenyl-(E)-hex-5-enoate 
• 133464-15-0 benzyl (S)-5-acetoxy-2-<(tert-butoxycarbonyl)amino>-4-oxopentanoate 
• 141362-38-1 phenylmethyl (S)-2-<<(1,1-dimethylethoxy)carbonyl>amino>-5-hexenoate 
• 94882-75-4 benzyl (2-t-butoxycarbonylamino)acrylate 
• 162536-47-2 (S)-2-tert-Butoxycarbonylamino-3-pyridin-4-yl-propionic acid benzyl ester 
• 239806-32-7 N^α-(tert-butoxycarbonyl)-C-(4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl)-L-tyrosine benzyl ester 

Relevant articles and documents

Development of Macrocyclic Peptides Containing Epoxyketone with Oral Availability as Proteasome Inhibitors

Macrocyclization has been frequently utilized for optimizing peptide or peptidomimetic-based compounds. In an attempt to obtain potent, metabolically stable, and orally available proteasome inhibitors, 30 oprozomib-derived macrocyclic peptides with structural diversity in their N-terminus and linker were successively designed and synthesized for structure-activity relationship (SAR) studies. As a consequence, the macrocyclic peptides with N-methyl-pyrazole (24p, 24x), imidazole (24t), and pyrazole (24v) as their respective N-termini exhibited favorable in vitro activity and metabolic stability, which translated into their potent in vivo proteasome inhibitory activity after oral administration. In particular, compound 24v, as the most distinguished one among this series, displayed excellent chymotrypsin-like (ChT-L, β5) inhibitory potency (IC50 = 16 nM), low nanomolar antiproliferative activity against all three of the tested cell lines, and superior metabolic stability in mouse liver microsome (MLM), as well as favorable inhibition against ChT-L compared to that of oprozomib in BABL/c mice following po administration at a comparatively low dose, thereby representing a promising candidate for further development.

Synthesis of new peptide nucleic acid monomer with glycylglycine backbone

New thymine peptide nucleic acid (PNA) monomer with glycylglycine backbone was prepared. This involved a key step of the coupling between iodinated serine (3) and 3-benzoylthymine.

Synthesis of all Three Regioisomers of Pyridylalanine

Pyridylalanines 4-6, differing from one another by the position of attachment on the heterocyclic ring were synthesized in moderate yield starting from serine and 2-, 3- and 4-bromopyridine respectively.