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The ease of installation of the protecting group follows the order: 1 o > 2 o > 3 o, allowing the least hindered hydroxyl group to be protected in the presence of more hindered hydroxyls. [ 4 ] Protection of equatorial hydroxyl groups can be achieved over axial hydroxyl groups by the use of a cationic silyl species generated by tert ...
Photolabile protecting groups bear a chromophore, which is activated through radiation with an appropriate wavelength and so can be removed. [6] For examples the o-nitrobenzylgroup ought be listed here. The rare double-layer protecting group is a protected protecting group, which exemplify high stability.
Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. The general structure is R 1 R 2 R 3 Si−O−R 4 where R 4 is an alkyl group or an aryl group. Silyl ethers are usually used as protecting groups for alcohols in organic synthesis.
The primary alcohols have general formulas RCH 2 OH; secondary ones are RR'CHOH; and tertiary ones are RR'R"COH, where R, R', and R" stand for alkyl groups. Subcategories This category has the following 3 subcategories, out of 3 total.
tert-Butyloxycarbonyl protecting group. The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium hydroxide:
The protection mechanism begins with the base deprotonating the alcohol group. Next, the deprotonated alcohol group attacks the silyl atom of the silyl halide compound. The halide acts as a leaving group and ends up in solution. A workup step follows to remove any excess base within the solution. The overall reaction scheme is as follows:
It is commonly abbreviated as TBSCl or TBDMSCl. It is a chlorosilane containing two methyl groups and a tert-butyl group. As such it is more bulky that trimethylsilyl chloride. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is used to protect alcohols in organic ...
This is useful because alcohols are poor leaving groups in S N 2 reactions, in contrast to the tosylate group. It is the transformation of alkyl alcohols to alkyl tosylates that allows an S N 2 reaction to occur in the presence of a good nucleophile. A tosyl group can function as a protecting group in organic synthesis. Alcohols can be ...