64519-41-1

Upstream product

• 67693-33-8 methyl-3-amino-2,3,6-tridesoxy-α-D-arabino-hexopyranoside 
• 407-25-0 trifluoroacetic anhydride 
• 18933-62-5 methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 17016-62-5 methyl-3-acetamido-2,3,6-tridesoxy-α-D-arabino-hexopyranoside 

Downstream Products

• 64429-67-0 N-((2R,3S,4R,6S)-3,6-Dihydroxy-2-methyl-tetrahydro-pyran-4-yl)-2,2,2-trifluoro-acetamide 
• 76753-26-9 methyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-arabino-hexopyranoside 
• 76793-36-7 1-O-acetyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-arabino-hexopyranose 
• 76793-37-8 1-O-acetyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-β-D-arabino-hexopyranose 
• 76753-25-8 2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-D-arabino-hexopyranose 
• 70629-86-6 7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-arabino-hexopyranosyl)daunomycinone 
• 70629-87-7 7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-β-D-arabino-hexopyranosyl)daunomycinone 

Relevant academic research and scientific papers

Stereoselective reactions. XX. Synthetic studies on optically active β-lactams. III. Stereocontrolled synthesis of chiral intermediate to (+)-thienamycin from D-glucose

A chiral key intermediate (19a) for the synthesis of (+)-thienamycin was synthesized starting from D-glucose. The enol ether 13, obtained from the ketone 11 by Horner-Wittig reaction, was transformed to the corresponding methyl ester 16 by pyridinium chlorochromate oxidation or by employing the Wacker process. The ester 16 was further converted to the β-lactam 19a, which is a useful chiral precursor to (+)-thienamycin.

HEMISYNTHESE DE NOUVEAUX GLICOSIDES ANALOGUES DE LA DAUNORUBICINE

Seven daunorubicin analogs containing α-L-, α-D-, and β-D-glicosidic linkages, in which the natural occuring sugar (L-daunosamine) was replaced by diastereomeric 3-amino-2,3,6-trideoxyhexoses (3-epi-L-daunosamine, D-acosamine, D-daunosamine, D-ristosamine, and 3-epi-D-daunosamine), were prepared.In all cases, glycosidation with daunomycinone was performed in the presence of p-toluenesulfonic acid starting from 1-O-acetyl-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoro-acetamidohexopyranoses (prepared from the corresponding methyl 3-amino-2,3,6-trideoxyhexopyranosides) or from 1,5-anhydro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamidohex-1-enitols (prepared from glycosals or pseudoglycals, the 3-amino group being introduced by substitution with sodium azide and subsequent reduction).Glycosidation was followed by removal of the protecting groups.