Silyl linker, solid phase

Nakamura K, Hanai N, Kanno M, Kobayashi A, Ohnishi Y, Ito Y, Nakahara Y. Design and synthesis of silyl ether-based linker for solid-phase synthesis of glycopeptides. Tetrahedron Lett 1999 40 515-518. 

Boehm TL, Showalter HDH. Development of a novel silyl ether linker for solid-phase organic synthesis. J Org Chem 1996 61 6498-6499. 

Newlander KA, Chenera B, Veber DF, Yim NCF Moore ML. Simple silyl linker for the solid phase organic synthesis of aryl-containing molecules. J Org Chem 1997 62 6726-6732. 

The galactosyl glycal 72 was bound to solid phase via a silyl ether linker. Epoxidation of the glycal using 2,2-dimethyldioxirane and subsequent electrophilic activation of the epoxide resulted in the glycosylation of 3,4-di-O-benzyl glucal 73. After acetylation of the product, the polymer-linked trisaccharide 74 was obtained. 

The first traceless linkers for arenes were silyl linkers. This linker type was used in the synthesis of a benzodiazepine library, a milestone in the solid-phase synthesis of small organic molecules (Scheme 6.1.9). Synthesis of the linker involves lithium-halogen exchange and, after chlorosilane attachment, coupling with an... 

The hydroboration of vinylsilane has been used to make 8-dimethylphenylsilylethyl ester linkers 10 (e.g., R = 4-CHO-C6H4) for solid-phase chemistry. In order to generate 8, polysytrene-divinylbenzene resin was lithiated and quenched with chlorodimethylvinylsilane. Hydroboration followed by an oxidative workup gave the silyl ethanol resin 9 (eq 5), which can be further functionalized and cleaved from the resin with a protodesilylation reaction using TFA. ... 

Boel996 Boehm, T.L. and Showalter, H.D.H., Development of a Novel Silyl Ether Linker for Solid-Phase Organic Synthesis, J. Org. Chem., 61 (1996) 6498-6499. 

Silyl linkers are very common in solid phase chemistry in their function as alcohol-protecting groups [332-338]. Cleavage from those silyl ether resins... 

In 2005, Ary a and co-workers reported on the stereocon-trolled solid-phase synthesis of a 90-membered library of indoline-alkaloid-like polycycles 41 and 42." These compounds are structurally related to a number of alkaloids such as vindoline, tabersonine, and yohimbine, and they could lead to compounds with similar or improved biological properties. Thus, chiral aminoindoline 36 was loaded via a silyl linker unit 37, deprotected, and reacted with an acid chloride to introduce the first point of diversity and to give 38. Treatment with piperidine removed the Fmoc group, and concomitant cyclization provided tricyclic... 

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