How do I get rid of Tbdms?
Various tert-butyldimethylsilyl ethers are easily removed in excellent yields by treatment with a catalytic amount of N-iodosuccinimide in methanol. This method allows a selective deprotection of TBDMS ethers of alcohols in the presence of TBDMS ethers of phenols.
What is silyl protection?
Silyl ethers are usually used as protecting groups for alcohols in organic synthesis. Since R1R2R3 can be combinations of differing groups which can be varied in order to provide a number of silyl ethers, this group of chemical compounds provides a wide spectrum of selectivity for protecting group chemistry.
What is a TBS group?
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What is the synthetic purpose of forming a silyl ether?
Silyl ethers are functional groups with Si covalently bonded to an alkoxy group. Silyl ethers are inert to many reagents that react with alcohols, so they serve as protecting groups in organic synthesis.
What is silylation reaction?
Silylation is the introduction of a (usually) substituted silyl group (R3Si) to a molecule. The process is the basis of organosilicon chemistry.
Are silyl ethers good leaving groups?
An alkoxy group is a notoriously poor leaving group. This is why silyl ethers make good protecting groups. They are exceptionally stable in base solution. In acid solution, they are easily removed to regenerate the original alcohol.
How do I remove SEM protecting groups?
SEM groups can be removed from protected heterocycles or nitrogen containing compounds using hydrochloric acid under refluxing conditions or at elevated temperature, while SEM protecting groups on nucleosides have been removed using tin tetrachloride at low temperature.
How do you protect a diol?
The most important method for the protection 1.2 diols or 1,3 diols is to convert them into a cyclic acetals or ketals. When the alcohols do not carry base labile group, they can be converted into their methyl ethers with suitable methylating agents i.e. diazomethane, methyl iodide etc.
How do you Deprotect alcohol?
The silyl ether protecting group can be removed by reaction with an aqueous acid or the fluoride ion. By utilizing a protecting group a Grignad reagent can be formed and reacted on a halo alcohol.
What do protecting groups do?
Protecting groups are used in synthesis to temporarily mask the characteristic chemistry of a functional group because it interferes with another reaction. A good protecting group should be easy to put on, easy to remove and in high yielding reactions, and inert to the conditions of the reaction required.
How do you do silylation?
The process involves the replacement of a proton with a trialkylsilyl group, typically trimethylsilyl (-SiMe3). Generally the substrate is deprotonated with a suitable strong base followed by treatment with a silyl chloride (e.g. trimethylsilyl chloride).
What is Bstfa?
N,O-Bis(trimethylsilyl)trifluoroacetamide (BSTFA) is a chemical compound that is used to derivatise labile groups such as hydroxyl on other chemicals, with the more stable trimethylsilyl group, which protects the labile group and allows the compound to be used for analytical purposes or as a chemical reagent for …