Acetylation of D-glucosamine catalysed by sulfuric acid and N-phthaloylation of the glucosyl acetate yielded 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranose. This gave the corresponding pure β-glucosyl chloride upon treatment with PCl5-BF3. An anomeric chlorination with thionyl chloride combined with the Lewis acids (ZnCl2, SnCl4 and BiCl3) resulted in an α/β anomer mixture.
JhaR., and DavisJ.T., Carbohydr. Res., 1995, 277, 125.
19.
ChaoC.S., ChenM.C., LinS.C., and MongK.K.T., Carbohydr. Res., 2008, 343, 957.
20.
PainterE.P., J. Am. Chem. Soc., 1953, 75, 1137.
21.
ÁvalosM., BabianoR., CintasP., HursthouseM.B., JiménezJ.L., LightM.E., PalaciosJ.C., and PérezE., Eur. J. Org. Chem., 2006, 657.
22.
ShodaS., Handbook of chemical glycosylation: advances in stereoselectivity and therapeutic relevance, ed. DemchenkoA.V.Wiley-VCH, Weinheim, 2008; pp 29–94.
23.
IbatullinF.M., and SelivanovS.I., Tetrahedron Lett., 2002, 43, 9577.
24.
EganL., SquiresT., and VercellottiJ., Carbohydr. Res., 1970, 14, 263.
25.
WangQ., and FuJ., ZhangJ., Carbohydr. Res., 2008, 343, 2989.
26.
GhoshR., ChakrabortyA., and MaitiS., Tetrahedron Lett., 2004, 45, 9631.