5456-63-3Relevant articles and documents
Improved Procedure for the Selective N-Debenzylation of Benzylamines by Diisopropyl Azodicarboxylate
Kroutil, Jiri,Trnka, Tomas,Cerny, Miloslav
, p. 446 - 450 (2007/10/03)
The selective deprotection of N-benzyl group was achieved in the presence of azido, O-benzyl, and N-tosyl groups in reactions of benzylamines derived from 1,6-anhydro-β-D-glucopyranose with diisopropyl azodicarboxylate (DIAD) in THF. The key role of this solvent and the reaction pathway are presented together with proven reaction intermediates.
SYNTHESIS OF (L)-DAUNOSAMINE AND RELATED AMINO SUGARS
Sammes, Peter G.,Thetford, Dean
, p. 111 - 124 (2007/10/02)
1-(2-Furyl)ethanol (6) has been converted into methyl (+/-)-daunosaminide (1) and methyl (+/-)-ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. (+/-)-Daunosamine (1) has been obtained more directly from the alcohol (10) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-1-ol as a model substrate.Asymmetric reduction of 2-acetylfuran (5) has given (S)-1-(2-furyl)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars (1), (2), and (3) from a cheap, non-carbohydrate precursor.
Opening of Epoxides with Trimethylsilyl Cyanide To Produce β-Hydroxy Isonitriles. A General Synthesis of Oxazolines and β-Amino Alcohols
Gassman, Paul G.,Guggenheim, Thomas L.
, p. 5849 - 5850 (2007/10/02)
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