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Synthesis of the n-benzoyl derivatives of L-arabino,L-xylo and L-lyxo (L-vancosamine) isomers of 2,3,6-trideoxy-3-C-methyl-3-aminohexose from a non-carbohydrate precursor

✍ Scribed by Giovanni Fronza; Claudio Fuganti; Piero Grasselli; Giuseppe Pedrocchi-Fantoni

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 256 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)92423-2

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✦ Synopsis

The synthesis of the N-benzoyi! derivatives of L-arabino ilO),L-xylo (13) and L-1~x0 -___ (L=vancosamine) (12) 2,3,6-trideoxy-3-C_methyl-3-minohexose from the (2g,3g) dioZ (1) prepared in fermenting bakers' yeast from cr-methyZcinnamaZdehyde and acetazdehyde is reported The 3-C-methyl branched amino sugars L-vancosamine (IZ,R= H) and its L-xylo isomer ---(13,R= H) occur as glycoside components in the glycopeptide antibiotics vancomycin I and A35512B2 In our interest in non-carbohydrate synthesis of deoxy-3 4 and deoxy-amino sugars, which are present in biologically active substances,we refer now on the synthesis of the N-benzoyl derivatives of the above mentioned amino-sugars and of the L-arabino isomer (IO), -___ using as source of chirality the (25,3R) methyl diol (I) prepared from a-methyl -5

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