What is a TBS group?

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How do I get rid of TBS protecting group?

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. B.

How do you remove acetyl protecting group?

Acetyl (Ac) group is common in oligonucleotide synthesis for protection of N4 in cytosine and N6 in adenine nucleic bases and is removed by treatment with a base, most often, with aqueous or gaseous ammonia or methylamine.

What is TBS in organic chemistry?

Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. Common silyl ethers are: trimethylsilyl (TMS), tert-butyldiphenylsilyl (TBDPS), tert-butyldimethylsilyl (TBS/TBDMS) and triisopropylsilyl (TIPS).

How do I Deprotect silyl?

Typical deprotection protocols for the removal of silyl ethers are acidic aqueous THF, or acidic methanol, alkaline aqueous solutions and sources of fluoride ion, most commonly tetra-n-butylammonium fluoride, TBAF, in various solvents.

What does Tbaf react with?

This TBAF/TsF reagent is compatible with many function groups including secondary alcohols, olefins, ketones, ethers, and esters. TsF is readily accessible from the reaction of tosyl chloride with KF in toluene water.

Is TBS a protecting group?

Silyl ethers are usually used as protecting groups for alcohols in organic synthesis. Common silyl ethers are: trimethylsilyl (TMS), tert-butyldiphenylsilyl (TBDPS), tert-butyldimethylsilyl (TBS/TBDMS) and triisopropylsilyl (TIPS).

What does a protecting group 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 much HF(OTF)4 is required for deprotection of TBS ether?

Hf (OTf) 4 exhibits exceptionally high potency in desilylations. Since the amounts of Hf (OTf) 4 required for the deprotection of 1°, 2°, 3° alkyl and aryl tert -butyldimethylsilyl (TBS) ethers range from 0.05 mol% to 3 mol%, a regioselective deprotection can be achieved.

Why is the reaction between TBSCl and THF selective?

However, the reaction in THF is made selective by two factors, kinetic deprotonation of the first anion AND the insolubility of the monoanion. At the initial addition of TBSCl, there is only a minor amount of monoanion in solution with the rest being in suspension.

What is the best deprotection method for TBS removal?

HF-pyridine, 10:1 THF:pyridine, 0 °C; an excellent deprotection; removes primary TBS groups within eight hours; reactions using HF must be run in plastic containers. TBAF, THF or 1:1 TBAF /AcOH, THF; TBDPS and TBS groups can be deprotected in the presence of one another under different conditions.

Can TBDPS and TBS groups be deprotected in the presence of one another?

TBAF, THF or 1:1 TBAF /AcOH, THF; TBDPS and TBS groups can be deprotected in the presence of one another under different conditions. ^ Corey, E. J.; Venkateswarlu, A. “Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives.”