1088780-64-6

Basic information

• Product Name: (S)-4-(4-iodophenoxy)butane-1,2-diol
• Synonyms: (S)-4-(4-iodophenoxy)butane-1,2-diol
• CAS NO: 1088780-64-6
• Molecular Weight: 308.116
• Mol File: 1088780-64-6.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-(4-iodophenoxy)butane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(4-iodophenoxy)butane-1,2-diol(1088780-64-6)
• EPA Substance Registry System: (S)-4-(4-iodophenoxy)butane-1,2-diol(1088780-64-6)

Safety Data

• Hazardous Substances Data: 1088780-64-6(Hazardous Substances Data)

Upstream product

• 540-38-5 p-Iodophenol 
• 1088780-69-1 (S)-4-(2-(4-iodophenoxy)ethyl)-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 1088780-57-7 (S)-4-(4-(pyren-1-ylethynyl)phenoxy)butane-1,2-diol 
• 1427039-95-9 (S)-4-(4-((trimethylsilyl)ethynyl)phenoxy)butane-1,2-diol 
• 1427039-96-0 (S)-4-(4-ethynylphenoxy)butane-1,2-diol 
• 1427039-97-1 (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol 
• 1427039-98-2 (S)-1-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2,3-b]quinoxalin-9-yl)ethynyl)phenoxy)butan-2-ol 
• 1427039-99-3 C₆₀H₆₅N₆O₆P 

Relevant articles and documents

Synthesis of a new intercalating nucleic acid 6H-indolo[2,3-b] quinoxaline oligonucleotides to improve thermal stability of Hoogsteen-type triplexes

A new intercalating nucleic acid monomer X was obtained in high yield starting from alkylation of 4-iodophenol with (S)-(+)-2-(2,2-dimethyl-1,3- dioxolan-4-yl)ethanol under Mitsunobu conditions followed by hydrolysis with 80% aqueous acetic acid to give a diol which was coupled under Sonogashira conditions with trimethylsilylacetylene (TMSA) to achieve the TMS protected (S)-4-(4-((trimethylsilyl)ethynyl)phenoxy)butane-1,2-diol. Tetrabutylammonium flouride was used to remove the silyl protecting group to obtain (S)-4-(4-ethynylphenoxy)butane-1,2-diol which was coupled under Sonogashira conditions with 2-(9-bromo-6H-indolo[2,3-b]quinoxalin-6-yl)-N,N- dimethylethanamine to achieve (S)-4-(4-((6-(2-(dimethylamino)ethyl)-6H-indolo[2, 3-b]quinoxalin-9-yl)ethynyl)phenoxy)butane-1,2-diol. This compound was tritylated with 4,4′-dimethoxytrityl chloride followed by treatment with 2-cyanoethyltetraisopropylphosphordiamidite in the presence of N,N′-diisopropyl ammonium tetrazolide to afford the corresponding phosphoramidite. This phosphoramidite was used to insert the monomer X into an oligonucleotide which was used for thermal denaturation studies of a corresponding parallel triplex.

High physiological thermal triplex stability optimization of twisted intercalating nucleic acids (TINA)

The structure of the monomer (R)-1-O-[4-(1-pyrenylethynyl)phenylmethyl] glycerol (1) in twisted intercalating nucleic acids (TINA) was optimized for stabilizing interactions between the intercalator and surrounding nucleobases when used as a triplex forming oligonucleotide (TFO). Enhancement of π-π interactions with nucleobases of the TFO was achieved by increasing the aromatic surface using the (R)-1-O-[4-(1-pyrenylethynyl)naphthylmethyl]glycerol monomer (2). Bulge insertion of 2 in the middle of a Hoogsteen-type triplex increased the triplex thermal stability, ΔTm = +2.0 °C compared with 1 at pH 7.2. Syntheses and thermal denaturation studies of triplexes and duplexes are described for three novel TINA monomers. The influence of π-π interactions, link length and the positioning of the ether in the linker in the TINA derivatives are described. The Royal Society of Chemistry 2008.