A new and efficient synthesis of monotritiomethyl iodide

Saljoughian, Manouchehr; Morimoto, Hiromi; Dorsky, Albert; Rapoport, Henry; Andres, Hendrik

doi:10.1002/jlcr.2580270705

Cited by 9 publications

(8 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…22 Ci/mmol, and 3 H NMR analysis revealed the same ratio of [3-3 H] cholest-5-ene isomers (70% 3-α-axial, 30% 3-β-equatorial) independent of the stereochemistry of the starting ester [109]. The deoxygenation and 2'-labeling of a Cribonucleoside by reductive elimination using tri-nbutyltin tritide in a one-pot reaction has recently been reported as a safe, simple, efficient and general method of labeling nucleosides at the 2'-position [109,110].…”

Section: Tritiodeoxygenationmentioning

confidence: 99%

Recent Developments in Tritium Incorporation for Radiotracer Studies

Saljoughian

Williams²

2000

CPD

Self Cite

View full text Add to dashboard Cite

The essential nature of rapid radiotracer synthesis very early in drug discovery programs has driven the need for better and more varied tritium incorporation methods. This review presents a summary of recent advances for tritium introduction via tritiated water, tritium gas, complex tritides, and a range of recently improved tritiation reagents. Access to a wider range of tritiated reagents (for tritioacetylation, tritioformylation, methylation, etc.) and commercial manifolds for the transfer and use of tritium gas is also discussed.

show abstract

Section: Tritiodeoxygenationmentioning

confidence: 99%

Recent Developments in Tritium Incorporation for Radiotracer Studies

Saljoughian

Williams²

2000

CPD

Self Cite

View full text Add to dashboard Cite

show abstract

“…In confirmation of deuterium labeling studies, 56 , 28b) independent of the stereochemistry of the starting ester (Scheme 24). 57 The deoxygenation and 2¢labeling of a C-ribonucleoside by reductive elimination using tributyltin tritide in a one-pot reaction has recently been reported as a safe, simple, efficient, and general method of labeling nucleosides at the 2¢-position 57,58 Another example of radical deoxygenation is shown in Scheme 25.…”

Section: Scheme 21mentioning

confidence: 99%

“…A new and efficient synthesis of high S.A. tritiated methyl iodide containing one atom of tritium per molecule has been reported from the tritiodehalogenation of chloromethyl esters. 58 The precursors for this reagent, chloromethyl p-phenylbenzoate or bis-chloromethyl terephthalate, were prepared by the condensation of the corresponding acid chlorides with paraformaldehyde in the presence of zinc chloride. Tritiodehalogenation of the precursors with tritium gas in the presence of Pd-C (10%) in DMF afforded the desired tritioesters.…”

Section: Monotritiomethyl Iodide From Estersmentioning

confidence: 99%

Synthetic Tritium Labeling: Reagents and Methodologies

Saljoughian¹

2002

Synthesis

Self Cite

View full text Add to dashboard Cite

This review presents a survey of new high specific activity tritium labeling reagents and methodologies developed in recent years and their applications to tritium labeling chemistry. The review is organized on the basis of reagent type, its development and applications. Emphasis is placed on the synthetic applications of the reagents and techniques that have an exceptionally high capability to produce high specific activity tritium labeled compounds. The focus of this review is on chemical labeling syntheses and does not include heterogeneous/homogeneous metal-catalyzed hydrogentritium exchange and biochemical reactions. 6 Conclusion

show abstract

“…, a series of 23-iodo-15-ketosterols 263a (283), alkyl and benzyl bromides 261,263 , N-iodoacetoxyphthalimide (284, see Section 4.4.8) 263b and, more recently, of a-bromo aldehyde 285, key intermediate in the synthesis [ 3 H]DCG-IV (286), a metabotropic glutamate receptor agonist labeled at a specific activity of 17.5 Ci/mmol 257 .The Bu 3 Sn 3 H-mediated tritiodeoxygenation of aryloxythiocarbonate and alkyldithiocarbonate esters of hydroxyl-substituted substrates (Barton deoxygenation) has been reported260,263 to be a good general method for the preparation of methylene-labeled compounds from the corresponding secondary alcohols. For example 2 0 -O-phenoxythio-…”

mentioning

confidence: 99%

Preparation of Tritium‐Labeled Compounds by Chemical Synthesis

2009

Preparation of Compounds Labeled With Tritium and Carbon‐14

View full text Add to dashboard Cite

In contrast to isotope exchange methods, which utilize the target compound or a late intermediate as substrate for labeling, chemical synthesis involves transformation of some precursor chemical with concurrent introduction of tritium. Four basic types of transformations are distinguished for discussion each in turn. They are catalytic tritiations (Section 4.1), which usually involve the reduction of a precursor compound using a catalyst and tritium gas; catalytic tritiolyses (Section 4.2), involving the replacement of functional groups by tritium, again using a catalyst and tritium gas; tritide reductions (Section 4.3), utilizing tritiated versions of hydridic reducing reagents; and the use of small tritiated building blocks (Section 4.4) in synthetic operations to construct target molecules.A phenomenon strongly relevant to the catalytic methods discussed in Sections 4.1 and 4.2, and of some relevance also for tritide chemistry (Section 4.3) is solvent exchange. Most catalytic tritiations and tritiolyses are conducted in solution, and a wide variety of solvents have been used, ranging from nonpolar ones to highly polar, hydroxylic media. The properties of the solvent, however, influence not only the course and rate of a heterogeneously catalyzed reaction, but also the extent to which solvent hydrogen may exchange with tritium gas as a side reaction and thereby dilute the isotope introduced into the substrate: solvent exchange. It is commonly recognized that the use of protic solvents for tritiations and tritiolyses increases the risk of obtaining products of less than maximal specific activity, although it is equally clear that such reactions often succeed without dilution of label. The crucial factor in each experiment is the relationship between the rate of the tritium-incorporation reaction and the rate(s) of any tritium-diluting reaction(s). It is documented that the rate of metal-catalyzed exchange between elemental hydrogen and water is significant, especially at low pH 1 , but little quantitative data are available to guide practice. Recently a turnover number of 17.3 h À1 was reported for the exchange between H 2 and 2 H 2 O catalyzed by 10% Pd/C at room temperature and a pressure of 1 atm 2 ; this is rapid enough to provide the basis for an economical method of catalytic deuterium exchange Preparation of Compounds Labeled with Tritium and Carbon-14 Rolf Voges, J. Richard Heys and Thomas Moenius

show abstract

A new and efficient synthesis of monotritiomethyl iodide

Cited by 9 publications

References 11 publications

Recent Developments in Tritium Incorporation for Radiotracer Studies

Recent Developments in Tritium Incorporation for Radiotracer Studies

Synthetic Tritium Labeling: Reagents and Methodologies

Preparation of Tritium‐Labeled Compounds by Chemical Synthesis

Contact Info

Product

Resources

About