Tritylation of alcohols under mild conditions without using silver salts

Shahsavari, Shahien; Chen, Jinsen; Wigstrom, Travis; Gooding, J. L.; Gauronskas, Alexander; Fang, Shiyue

doi:10.1016/j.tetlet.2016.07.062

Cited by 13 publications

(8 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In Figure , a close-up of the 1 H NMR spectra of the Mtt-methyl group in its bound and free form is shown at different TFA concentrations in CDCl 3 . At higher TFA concentrations, the signals are low-field-shifted, which is in agreement with our observations of the 1 H NMR spectra of Mtt-Cl under the same conditions (Figure S68) as well as reported trityl derivatives. , The two different peaks for the free Mtt-methyl group can be explained by an equilibrium with TFA (Figure A), which was described previously. , …”

supporting

confidence: 93%

“…39,40 The two different peaks for the free Mtt-methyl group can be explained by an equilibrium with TFA (Figure 2A), which was described previously. 41,42 To test the applicability of our Mtt-protected compounds for SPPS, we next synthesized a hairpin polyamide [ImPyPyIm-γ-PyImImPy-β-Dp (1)] containing all of them (Figure 1). For comparison, we prepared the same sequence using the Fmoc-protected compounds, too.…”

mentioning

confidence: 99%

See 1 more Smart Citation

4-Methyltrityl-Protected Pyrrole and Imidazole Building Blocks for Solid Phase Synthesis of DNA-Binding Polyamides

Heinrich

Vázquez

2020

Org. Lett.

View full text Add to dashboard Cite

DNA-binding polyamides are synthetic oligomers of pyrrole/imidazole units with high specificity and affinity for double-stranded DNA. To increase their synthetic diversity, we report a mild methodology based on 4-methyltrityl (Mtt) solid phase peptide synthesis (SPPS), whose building blocks are more accessible than the standard Fmoc and Boc SPPS ones. We demonstrate the robustness of the approach by preparing and studying a hairpin with all precursors. Importantly, our strategy is orthogonal and compatible with sensitive molecules and could be readily automated.

show abstract

supporting

confidence: 93%

mentioning

confidence: 99%

4-Methyltrityl-Protected Pyrrole and Imidazole Building Blocks for Solid Phase Synthesis of DNA-Binding Polyamides

Heinrich

Vázquez

2020

Org. Lett.

View full text Add to dashboard Cite

show abstract

“…Lcaa-CPG (pore size 497 Å) was purchased from Prime Synthesis. Compounds 12a–e were prepared according to the reported procedure. ,, Thin layer chromatography (TLC) was performed using Sigma-Aldrich TLC plates, silica gel 60F-254 over glass support, 250 μm thickness. Flash column chromatography was performed using SiliCycle silica gel, particle size 40–63 μm.…”

Section: Methodsmentioning

confidence: 99%

Sensitive Oligodeoxynucleotide Synthesis Using Dim and Dmoc as Protecting Groups

et al. 2019

Self Cite

View full text Add to dashboard Cite

In traditional oligodeoxynucleotide (ODN) synthesis, phosphate groups are protected with the 2-cyanoethyl group, and amino groups are protected with acyl groups. At the end of ODN synthesis, deprotection is achieved with strong bases and nucleophiles. Therefore, traditional technologies are not suitable for the synthesis of ODNs containing sensitive functionalities. To address the problem, we report the use of Dim and Dmoc groups, which are based on the 1,3-dithian-2-yl-methyl function, for phosphate and amine protection for the solid phase ODN synthesis. Using the new Dim–Dmoc protection, deprotection was achieved under mild oxidative conditions without using any strong bases and nucleophiles. As a result, the new technology is suitable for the synthesis of ODNs containing sensitive functions. To demonstrate feasibility, seven 20-mer ODNs including four that contain sensitive ester and alkyl chloride groups were synthesized, purified with RP HPLC, and characterized with MALDI-TOF MS and enzyme digestion essays. High purity ODNs were obtained.

show abstract

“…However, the yield of 10 dropped ever lower due to the formation of more diDMT-protected side product. In addition, we also tested the reactions with a catalytic amount of DMAP, 2 equiv of DIPEA, and a new tritylation reagent, DMT-trifluoroacetate (Table 1, Entry 4-7) [28]. However, none of these conditions led to improved results.…”

Section: Synthesis Of Cyanoethyl-protected 5hmdc Phosphoramidite (1)mentioning

confidence: 99%

An Improved Approach for Practical Synthesis of 5-Hydroxymethyl-2′-deoxycytidine (5hmdC) Phosphoramidite and Triphosphate

et al. 2022

View full text Add to dashboard Cite

5-Hydroxymethyl-2′-deoxycytidine (5hmdC) phosphoramidite and triphosphate are important building blocks in 5hmdC-containing DNA synthesis for epigenetic studies. However, efficient and practical methods for the synthesis of these compounds are still limited. The current research provides an intensively improved synthetic method that enables the preparation of commercially available cyanoethyl-protected 5hmdC phosphoramidite with an overall yield of 39% on 5 g scale. On the basis of facile and efficient accesses to cyanoethyl protected-5hmdU and 5hmdC intermediates, two efficient synthetic routes for 5hmdC triphosphate were also developed.

show abstract

Tritylation of alcohols under mild conditions without using silver salts

Cited by 13 publications

References 32 publications

4-Methyltrityl-Protected Pyrrole and Imidazole Building Blocks for Solid Phase Synthesis of DNA-Binding Polyamides

4-Methyltrityl-Protected Pyrrole and Imidazole Building Blocks for Solid Phase Synthesis of DNA-Binding Polyamides

Sensitive Oligodeoxynucleotide Synthesis Using Dim and Dmoc as Protecting Groups

An Improved Approach for Practical Synthesis of 5-Hydroxymethyl-2′-deoxycytidine (5hmdC) Phosphoramidite and Triphosphate

Contact Info

Product

Resources

About