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Specifically, the 2-tetrahydropyranyl (THP) group is a common protecting group for alcohols. [5] [6] Alcohols react with 3,4-dihydropyran to give 2-tetrahydropyranyl ethers. These ethers are resilient to a variety of reactions. The alcohol can later be restored by acid-catalyzed hydrolysis. This hydrolysis reforms the parent alcohol as well as ...
Boronic acids and esters are classified depending on the type of carbon group (R) directly bonded to boron, for example alkyl-, alkenyl-, alkynyl-, and aryl-boronic esters. The most common type of starting materials that incorporate boronic esters into organic compounds for transition metal catalyzed borylation reactions have the general ...
The general structure of a boronic acid, where R is a substituent. A boronic acid is an organic compound related to boric acid (B(OH) 3) in which one of the three hydroxyl groups (−OH) is replaced by an alkyl or aryl group (represented by R in the general formula R−B(OH) 2). [1]
An organic group's migration propensity depends on its ability to stabilize negative charge: alkynyl > aryl ≈ alkenyl > primary alkyl > secondary alkyl > tertiary alkyl. [32] Bis(norbornyl)borane and 9-BBN are often hydroboration reagents for this reason — only the hydroborated olefin is likely to migrate upon nucleophilic activation.
The mechanism of organotrifluoroborate-based Suzuki-Miyaura coupling reactions has recently been investigated in detail. The organotrifluoroborate hydrolyses to the corresponding boronic acid in situ, so a boronic acid can be used in place of an organotrifluoroborate, as long as it is added slowly and carefully. [7] [8]
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 Petasis reaction exhibits high degrees of stereocontrol when a chiral amine or aldehyde is used as a substrate. When certain chiral amines, such as (S)-2-phenylglycinol, are mixed with an α-keto acid and vinyl boronic acid at room temperature, the corresponding allylamine is formed as a single diastereomer.
Names of acyl groups of ribonucleoside monophosphates such as AMP (5′-adenylic acid), GMP (5′-guanylic acid), CMP (5′-cytidylic acid), and UMP (5′-uridylic acid) are adenylyl, guanylyl, cytidylyl, and uridylyl respectively. In phospholipids, the acyl group of phosphatidic acid is called phosphatidyl-. Finally, many saccharides are acylated.