ORGLIST: Reagarding 1, 5 dicarbonyl sugar preparation and its reductive amination

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From: shailesh patel m (shailptl$##$rediffmail.com)
Date: Wed Nov 30 2005 - 09:49:02 EST


Deal all, I have been working in the project involving Tetra O-benzyl Deo=
xynojirimycin (Bn4DNJ)synthesis. Its synthesis includes double Pftizne=
r-Moffat oxidation as given in the paper "Synthesis, 1999, No. 4, 571-573"=

eaction. I have tried swern oxidation as well.Reaction was not going to com=
pletion when I used reported quantity of DMSO/TFAA. Increasing quantity did=
 not make much difference. 2) Purification was really very very turf.=
 Can anybody suggest me the method of purification in detail which will giv=
e me satisfactory results.I am using the silica 60/120 mesh(Ethyl acetate :=
 Hexane)(5:95)everything comes out on conventional chromatography. I have t=
ried neutral silica and Alumina as well.No separation and huge loss in the =
column purification with this protocol. 3) Generally for the sugar der=
ivative which stationary phase is used ? For your ready reference I ha=
ve attached scheme involved for your ready reference. Looking for your=
 co-operation. Shailesh


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