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 Deoxynojirimycin (Bn4DNJ)synthesis. Its synthesis includes double Pftizner-Moffat oxidation as given in the paper "Synthesis, 1999, No. 4, 571-573" I am facing problem like 1) Oxidation was not giving clear cut reaction. I have tried swern oxidation as well.Reaction was not going to completion 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 give me satisfactory results.I am using the silica 60/120 mesh(Ethyl acetate : Hexane)(5:95)everything comes out on conventional chromatography. I have tried neutral silica and Alumina as well.No separation and huge loss in the column purification with this protocol. 3) Generally for the sugar derivative which stationary phase is used ? For your ready reference I have attached scheme involved for your ready reference. Looking for your co-operation. Shailesh



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