174175-08-7

Upstream product

• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 
• 174020-80-5 methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranosid-3-ulose diphenylphosphinamide 
• 174020-81-6 methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose diphenylphosphinamine 
• 63598-32-3 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranosid-3-ulose oxime 

Downstream Products

• 81090-83-7 methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside 
• 81090-82-6 methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside 
• 127853-68-3 methyl 4,6-O-benzylidene-3-trifluoroacetamido-2,3-dideoxy-α-D-ribo-hexopyranoside 

Relevant academic research and scientific papers

Carbohydrate N-phosphinyl imine derivatives: synthesis and conversion to amino sugars

- Keywords: Imines; N-phosphinyl; Sugars, amino, synthesis; Oximes

A PRACTICABLE SYNTHESIS OF N-TRIFLUOROACETYL-L-DAUNOSAMINE FROM D-GlUCOSE

A synthesis of the N-trifluoroacetyl derivative of L-daunosamine, the glucidic component of adriamycin and daunomycin, two antibiotics with proved antineoplastic activity, is described starting from D-glucose, an inexpensive carbohydrate source.The synthetic sequence involves the stereoselective introduction of the C(3) amino group and the inversion at C(5), obtained by the stereospecific hydrogenation of a 5-methylenepyranose derivative, to flip from the D over the L series.