Organic-fluorous phase switches: A fluorous amine scavenger for purification in solution phase parallel synthesis

The synthesis of the fluorous amine scavenger [(C6F13CH2CH2)3SiCH2CH2CH2]2NH and its successful application in the automated solution phase parallel synthesis of a urea library are described. Ureas were made by robotic synthesis from organic amines and excess isocyanates. The amine scavenger reacts with excess isocyanate, and the fluorous tag serves to solubilize the resulting adduct in the fluorous phase so it can be removed by fluorous-organic extraction. Organic urea products are isolated in high yields and purities after liquid-liquid extraction. Preliminary biological evaluation shows that several of the ureas have ion channel modulation abilities. In contrast to polymer and ionic quenching methods, the fluorous quench works whether the product is soluble or insoluble in the reaction medium, and ionizable functional groups are tolerated in the products

Fluorous triphasic reactions: Transportative deprotection of fluorous silyl ethers with concomitant purification [11]

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A novel stereoselective one-pot conversion of alcohols into alkyl halides mediated by N,N '-diisopropylcarbodiimide

Alcohols can be converted in high yields to the corresponding alkyl halides in a one-pot procedure via the corresponding O-alkylisourea; very short reaction times are possible when microwave irradiation is used

Isoureas: versatile synthetic intermediates

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Short synthesis of enantiopure C-2-Symmetric 1,2 : 4,5-diepoxypentane and "Pseudo"-C-2-symmetric 3-azido-1,2 : 4,5-diepoxypentane from arabitol

On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C-2-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C-2-symmetrical 1,2:4,5-bis-epoxypentane building block I is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis

Full and partial differentiation of tris-1,1,1-(hydroxymethyl)ethane via direct and indirect methodology

Tris-1,1,1-(hydroxymethyl)ethane 1 was converted to a series of mono- and disubstituted derivatives. An indirect protocol for the differentiation of the alcohol groups was employed for the synthesis of partially and fully differentiated 1 containing a protected aldehyde unit. Complete differentiation of the alcohol groups was also achieved using a direct strategy (two steps from 1). The first synthesis of 1,3-dialclehydes derived from 1 is reported in two steps