ORGLIST:Phosphitylation of cyclic alcohol compound

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From: mohd zulkefeli (mzmj$##$hiroshima-u.ac.jp)
Date: Fri Apr 16 2004 - 06:09:16 EDT


Dear members,

I am trying to phosphitylate a cyclic alcohol compound using
dibenzyl-N,N-diisopropylphosphoramidite. In the reference papers which used
this phosphoramidite, the condition of reaction is always as react the
cyclic alcohol compound in the present of 1H-tetrazole in dichloromethane
solvent with dibenzyl-N,N-diisopropylphosphoramidite and after that the
oxidation by m-CPBA at -40 degree to get the O-dibenzooxyphosphono group
with a yield at average more than 80%. But for my reaction, the yield is
always low (about less than 20%) and it is always a question to me what is
going wrong with my reaction. Is anybody there who ever do this kind of
reaction who can tell me about the method or condition related to this
phosphitylation?

Thanks in advance!

M.zulkefeli

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