478183-68-5

Basic information

• Product Name: BOC-3-IODO-D-TYR-OH
• Synonyms: N-ALPHA-BUTOXYCARBONYL-3-IODO-D-TYROSINE;BOC-D-TYR(3-I)-OH;BOC-D-3-IODOTYROSINE;BOC-3-IODO-D-TYR-OH;BOC-3-IODO-D-TYROSINE;(R)-2-(tert-butoxycarbonylamino)-3-(4-hydroxy-3-iodophenyl)propanoic acid;(Tert-Butoxy)Carbonyl D-Tyr(3-I)-OH
• CAS NO: 478183-68-5
• Molecular Formula: C14H18INO5
• Molecular Weight: 407.2
• Product Categories: Amino Acid Derivatives
• Mol File: 478183-68-5.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 0-5°C
• CAS DataBase Reference: BOC-3-IODO-D-TYR-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-3-IODO-D-TYR-OH(478183-68-5)
• EPA Substance Registry System: BOC-3-IODO-D-TYR-OH(478183-68-5)

Safety Data

• Hazardous Substances Data: 478183-68-5(Hazardous Substances Data)

Usage

General Description

BOC-3-IODO-D-TYR-OH is a chemical compound with the molecular formula C16H22I2N2O4. It is commonly used as a building block in the synthesis of peptides and pharmaceuticals. BOC-3-IODO-D-TYR-OH contains a protected amino acid, which means the hydroxyl group and the alpha-amino group are both protected with a tert-butoxycarbonyl (BOC) group. The addition of the 3-iodo group makes this compound useful for introducing radioiodine into peptides for imaging or therapy purposes. BOC-3-IODO-D-TYR-OH is considered a versatile intermediate in organic synthesis and plays a critical role in the development of various bioactive molecules.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 70-78-0 3-Iodo-L-tyrosine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 556-02-5 tyrosine 
• 25799-58-0 (R)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 60-18-4 L-tyrosine 
• 79677-58-0 2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride 
• 3978-80-1 Boc-Tyr-OH 
• 119336-08-2 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate 

Downstream Products

• 160531-32-8 (R)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)propanoic acid 
• 122886-21-9 (R)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)-2-(methylamino)propanoate 
• 333354-23-7 (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester 
• 333354-37-3 (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid 
• 333354-24-8 (2S,4S,6R,7S,9S)-9-[(R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionyloxy]-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid tert-butyl ester 
• 333354-25-9 (3R,9S,11S,13R,14S,16S)-14-Hydroxy-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione 
• 622336-82-7 (S)-2-((tert-butoxycarbonyl)amino)-3-(3-iodo-4-methoxyphenyl)propanoic acid 

Relevant articles and documents

Genetic incorporation of a metal-chelating amino acid as a probe for protein electron transfer

ET encounters jellyfish: Through the incorporation of the metal-chelating amino acid pyTyr into green fluorescent protein (GFP) from jellyfish, photoinduced electron transfer (ET) from the GFP chromophore to a bound Cu II ion was shown to occur within one nanosecond in a distance-dependent manner. The crystal structure of GFP with pyTyr at a specific position shows the structural basis for the nanomolar binding affinity of pyTyr to CuII ions. Copyright

Synthesis of Pentacyclic Framework of Herquline A

The highly strained bowl-shaped pentacyclic structure of herquline A has rendered it one of the most difficult problems in organic synthesis yet to be solved. The challenges associated with the synthesis of herquline A have been well documented in four Ph.D. dissertations and in multiple reports regarding syntheses of its structurally simpler congeners. Herein, we report the construction of the pentacyclic core of herquline A that contains both N10?C2 and C3?C3′ bonds. The key for success was the development of the tandem aza-Michael addition/enolate capture protocol that set the stage for subsequent palladium catalyzed C3(sp2)?C3′(sp2) coupling reaction. Ensuing oxidative dearomatization of the left aryl ring allowed the formation of the pentacyclic diketone core of herquline A.

Concise Total Synthesis of Herqulines B and C

A simple total synthesis of herqulines B and C is reported, modeled on the reductive biosynthesis reported previously by other researchers. Commencing from tyrosine, these alkaloids were fashioned through a dimerization, macrocyclization, and four consecu