76793-59-4

Basic information

• Product Name: 7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-β-L-arabino-hexopyranosyl>daunomycinone
• CAS NO: 76793-59-4
• Molecular Weight: 772.642
• Mol File: 76793-59-4.mol

Chemical Properties

• CAS DataBase Reference: 7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-β-L-arabino-hexopyranosyl>daunomycinone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-β-L-arabino-hexopyranosyl>daunomycinone(76793-59-4)
• EPA Substance Registry System: 7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-β-L-arabino-hexopyranosyl>daunomycinone(76793-59-4)

Safety Data

• Hazardous Substances Data: 76793-59-4(Hazardous Substances Data)

Upstream product

• 21794-55-8 (+)-Daunomycinone 
• 72384-25-9 1,5-anhydro-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-D-xylo-hex-1-enitol 
• 73891-04-0 2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-L-arabino-hex-1-enitol 
• 14218-08-7 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide 
• 73864-38-7 2,3,6-tridesoxy-3-(trifluoroacetamido)-L-arabino-hex-1-enitol 
• 73864-37-6 3-amino-1,5-anhydro-2,3,6-tridesoxy-L-arabino-hex-1-enitol 
• 122-04-3 4-nitro-benzoyl chloride 
• 34820-21-8 1,5-anhydro-3,4-di-O-benzoyl-2,6-didesoxy-L-arabino-hex-1-enitol 
• 76739-66-7 3,4-di-O-acetyl-D-rhamnal 
• 61819-51-0 methyl-4-O-benzoyl-2,3,6-tridesoxy-α-D-threo-hex-2-enopyranoside 
• 76793-56-1 1,5-anhydro-2,3,6-tridesoxy-3-trifluoroacetamido-D-xylo-hex-1-enitol 
• 33648-02-1 methyl-4-O-acetyl-2,3,6-tridesoxy-α-D-erythro-hex-2-enopyranoside 
• 73864-37-6 3-amino-1,5-anhydro-2,3,6-tridesoxy-D-xylo-hex-1-enitol 
• 33648-04-3 methyl-4-O-acetyl-2,3,6-tridesoxy-α-D-threo-hex-2-enopyranoside 

Relevant articles and documents

SUBSTITUTIONS D'ESTERS ALLYLIQUES: PREPARATION DE GLYCALS AMINES EN C-3 ET ETUDE DE LEUR GLYCOSIDATION ACIDO-CATALYSEE. APPLICATION A L'HEMISYNTHESE DE GLYCOSIDES DU GROUPE DES ANTHRACYCLINES

3-Amino-1,5-anhydro-2,3,6-trideoxy-L-arabino- and -L-ribo-hex-1-enitol were prepared by substitution of the allylic ester function of 1,5-anhydro-3,4-di-O-benzoyl-2,6-dideoxy-L-arabino-hex-1-enitol with sodium azide, followed by reduction with lithium aluminium hydride.Glycosidation was performed with various alcohols, in particular daunomycinone.In the latter case, the partial synthesis of 4'-epi- and 3',4'-epi-daunorubicines was accomplished in three major steps.

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.