Selective acetylation of per-O-TMS-protected monosaccharides.
Selective acetylation of various per-O-TMS-protected carbohydrates has been accomplished. Using a protecting group exchange strategy and microwave assistance, monosaccharides (glucose, galactose, and mannose) can be selectively acetylated producing either the 6-O-monoacetate or 1,6-O-diacetylated species. This new class of molecules can be deprotected without migration of the acetyl groups, providing useful synthetic intermediates. To demonstrate the scope of the reaction, the methodology was successfully extended to TMS-protected ceramide.
Witschi
Mark A
MA
Department of Chemistry, University of California, Davis, 1 Shields Avenue, Davis, California 95616, USA.
Gervay-Hague
Jacquelyn
J
D000107:Acetylation; D002518:Ceramides / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D002518:Ceramides; D009005:Monosaccharides; D014297:Trimethylsilyl Compounds
Nature. 2007 Apr 19;446(7138):896-9
17443183
Org Lett. 2001 Jun 28;3(13):2081-4
11418054
Acc Chem Res. 2010 Aug 17;43(8):1144-53
20496888
J Comb Chem. 2008 Jan-Feb;10(1):79-87
18062672
J Org Chem. 2001 Dec 14;66(25):8395-401
11735517
J Org Chem. 2010 Aug 6;75(15):4891-8
20387787
Chem Commun (Camb). 2007 Jun 21;(23):2336-8
17844738
Org Lett. 2004 Mar 18;6(6):945-8
15012071