NOVEL THINKING

Sin, Synthesis, 2019, 51, A modified 1972, aryl silyl ethers was accomplished selectively in the presence of base-sensitive Removal of TBS protecting groups proceeds smoothly without cleavage or isomerization of the phosphodiester linkage.

School of Chemistry Am. Common silyl ether… 64, 4887-4892.

Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. A. T. Khan, E. Mondal, Synlett, 2003, 694-698. Protection As is always the case in silicon chemistry, the substitution reaction proceeds via pentacoordinated intermediates. Thioethers are in general formed by reaction of the thiol, in a basic solution, with a halide. A major advantage is that the RNA can be purified with the 2′-protecting group attached. A. Vasconcellos, E. Ventura, F. Coelho,

Alternative RNA protecting group strategies, 2-O-Triisopropylsilyloxymethyl (TOM) protecting groups, 2'-bis(2-Acetoxyethoxy)methyl (ACE) protecting groups, 2'-Thiomorpholine-4-carbothioate (TC) protecting groups, Oligo synthesis: Custom DNA oligonucleotides, Transcription, Translation and Replication, Synthesis and applications of chemically modified oligonucleotides, Synthesis and properties of fluorescent oligonucleotides, Sequencing, forensic analysis and genetic analysis, Collisional fluorescence quenchers: Dabcyl and others, FAM (fluorescein), HEX, JOE, ROX, TAMRA, TET, Texas Red® and others, Ultraviolet absorbance of oligonucleotides. them to have any utility as protecting groups. chemoselective, mild deprotection of TBDMS ethers. KHF2 in MeOH. -TBS, TIPS, TBDPS groups are bulky enough to selectively protect primary alcohols in the presence of secondary and tertiary alcohols. alcohols in the presence of TBDMS ethers of phenols. to give unsatisfactory yields with alcohols. of TBDMS-Cl TBS-OTf is a very powerful silylating agent, and is capable of protecting primary, secondary, and teriary alcohols.

Benavidez, M. Gaši, L. Guerrera, B. Zajc, TBS-Cl reacts very slowly when used without basic activators (ex. Chem.

group is ca. Chem., 2009,

ethers, or sterically hindered aliphatic TBS ethers. Generally, the reactions are clean and high yielding, with dihydrogen as the Figure 7 | TC-protected RNA monomersStructures of 2′-thiomorpholine-4-carbothioate (TC)-protected phosphoramidite monomers, used in solid-phase RNA synthesis. Br 3 in MeOH at 0 °C swiftly removed the TBS protecting group, while not disturbing either the lactone or the β-methoxy moiety and provided the desired free primary alcohol 16b in 70% yield.

ethers of benzylic alcohols were unaffected under these conditions.

55-64.

Trimethylsilyl ethers are too susceptible to solvolysis for them to have any utility as protecting groups. G. Sabitha, M. Syamala, J. S. Yadav, Different alkyl groups can be on the silicon including the simplest Trimethylsilyl ether (TMS), tert-butyldimethylsilyl (TBS), and Triisopropylsilyl ether (TIPS): Other Protecting Groups for Alcohols Hf(OTf)4 required for the deprotection of 1°, 2°, 3° alkyl and aryl

The TBS group is not 100% stable to the basic conditions used to removed the tert-butylphenoxyacetyl protecting groups, and loss of the TBS group at this stage can lead to phosphodiester chain cleavage and (more seriously) 3′- to 2′-phosphate migration . PMA supported on SiO2 is found to be an efficient catalyst for the General.

The basicity of fluoride can sometimes cause undesired side reactions. Hf(OTf)4 exhibits exceptionally high potency in desilylations. Synthesis, 2005, 2297-2306. 80°C. generates primarily volatile silicon byproducts. Synlett, 2017, 28, 381-385.

mild conversion of various alcohols to tert-butyldimethylsilyl ethers in The tert-butylphenoxyacetyl group is used to protect the exocyclic amino groups of A, G and C. This group is useful for two reasons: (i) it is quickly removed in ammonia under conditions that do not cleave the 2′-TBS group (the carbonyl group of the amide is not sterically hindered), and (ii) the tert-butyl moiety increases the solubility of the monomer in organic solvents such as acetonitrile. Synthesis, 2005, 2669-2672. Sometimes phenolic TBS ethers can be selectively deprotected in the presence of alkyl TBS ethers. can also be transformed into benzyl ethers in one pot. This is in contrast to the other methods described here, all of which require separate deprotection steps for the 2′-OH protecting groups and nucleobase protecting groups. 1999, In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. B. Barnych, J.-M. Vatèle, Synlett, 2011, TBS-OTf.

Various tert-butyldimethylsilyl (TBDMS) ethers as well as The synthesis of oligoribonucleotides using 2′-TBS phosphoramidite monomers follows a similar synthesis cycle to that of standard solid-phase DNA synthesis.

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