Sorry for my poor English.

I'm not major in organic so that I'm sure there are a lot of mistakes or stupidness in my description.So that please give me as much critique and suggestions as you can.Great thanks.

The problem is to transfer one of the hydroxyl group (-OH) to azide(-N3) on the glucosamine.

This is the structure of glucosamine.

The target hydroxyl group is that on the -CH2OH

Till now,with my poor knowledge on organic,I have made the following plan:

1,Let the glucosamine have a reaction with methanol in acid to produce methyl 2-aminoglucoside.

2,Disssolve the methyl 2-aminoglucoside in pyridine and add some tosyl chloride or 2,6-dimethylphenylsulfonyl chloride to transfer the target -OH to -Cl.

3,Dissolve the product in DMF and add some NaN3 to transfer the -Cl to -N3.

I'm not major in organic so that I produce this plan only by referring to papers.So that is it reasonable?Or can you give me some good suggestions or is there any improvement to it?Will there be some critical or troublesome side-reactions?Great thanks.

Besides,I still have no idea of how to separate the product from the reactant.So that I'll be greatly appreciated if you can also give me some ideas on the separation.