Home
Resources
Publications
Regioselectively Trisilylated Hexopyranosides Through Homogeneously Catalyzed Silane Alcoholysis

Regioselectively Trisilylated Hexopyranosides Through Homogeneously Catalyzed Silane Alcoholysis

Mee-Kyung Chung, Marcel Schlaf

J Am Chem Soc. 2005 Dec 28;127(51):18085-92.

PMID: 16366560

Abstract:

The iridium complex [Ir(COD)(PPh3)2]+ SbF6- reacts with tert-butyldimethylsilane in DMA to form [IrH2(Sol)2(PPh3)2]+ SbF6-, which is an active catalyst for the regioselective di- and trisilylation of a series of representative methyl hexopyranosides, beta-1,6-anhydrohexopyranosides and 1,3,5-O-methylidene inositol. The corresponding 2,3,6- and 2,4,6-silylated glycosides are obtained in a separable mixture of 47-89% (2,3,6-isomers) and 9-25% (2,4,6-isomers) yield in a single-pot reaction. The 2,4-disilylated derivatives of mannosan, galactosan, and 1,3,5-O-methylidene inositol as well as persilylated levoglucosan are accessible in >85% yield by this method. The homogeneous nature of the catalysts is a prerequisite for the effective di-/trisilylation, as nanoparticle colloid catalysts generated in situ from Pd2(dba)3 (approximately 1.5 nm average particle size) or Ru2Cl5(MeCN)7 (approximately 0.65 nm average particle size) result in only low yields.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP29681570	tert-Butyldimethylsilane		29681-57-0	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: