67737-59-1Relevant articles and documents
The total synthesis of L-daunosamine
Jurczak, Janusz,Kozak, Janusz,Golebiowski, Adam
, p. 4231 - 4238 (2007/10/02)
N,O-Dibenzyl-N-tert-butoxycarbonyl-L-homoserinal (7), obtained from L-aspartic acid, reacts with vinylmagnesium chloride to afford with high stereoselectivity compound 6 which is subsequently transformed into the derivative of L
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.