Multigram Synthesis of Well-Defined Extended Bifunctional Polyethylene Glycol (PEG) Chains

Abstract

A series of novel, well-defined, unsymmetrical poly(ethylene glycol) chains of the type X(OCH(2)CH(2))(n)()Y (where X = protecting group; Y = nucleofuge or a different protecting group; n = 3, 6, 9, 12, 15, 18, and 24) were prepared in high yields by applying orthogonal protecting groups. The purity of the compounds was fully verified by elemental and high-resolution mass spectrometry analyses.

Probing the Effects of Hydrophilic Branch Size, Distribution, and Connectivity in Amphiphilic Polyethylene

“…For this to occur, we believe, the PEG branch must be inducing a fold in the PE backbone, thereby allowing for the clustering of the branches and allowing the backbone to form small, isolated paraffin-like crystallites ( Figure 1). While the domain sizes that would result from this model are quite small in comparison to other amphiphilic PE-co-PEG block and graft copolymer systems, [11][12][13][16][17][18] this behavior is well documented for alternating block oligomers [19][20][21] of PEG and PE having blocks of similar size to the branch-tobranch distance and PEG branch lengths of our polymers.…”

Synthetic Multimeric Heptyl Mannosides as Potent Antiadhesives of Uropathogenic Escherichia coli

“…A tosyl group was introduced in compound 9 using pTsCl, KI and Ag 2 O leading to 11 in 89 % yield. [16] Subsequent reaction with compound 9 in the presence of NaH [17] allowed the isolation of diazido-EG 14 in 59 % yield. A similar procedure was used for the synthesis of tri-and tetraazido derivatives 15 and 16 starting from 1,1,1-tris(hydroxymethyl)ethane 12 and pentaerythritol 13, respectively.…”

Synthesis of novel fluorous surfactants for microdroplet stabilisation in fluorous oil streams

“…In order to create molecules 14-16 possessing hexaethylene glycol head groups it was first necessary to achieve either monoprotection or monoactivation of a terminal hydroxyl group on the hexaethylene chain therefore allowing for selective modifications with fluorous derivatives 1, 2 and 3 [31]. Activation of hexaethyleneglycol 29 was achieved by mono-tosylation, whereby the diol was reacted with silver (I) oxide and potassium iodide in the presence of tosyl chloride to afford 30 in 67% yield (Fig.…”