Synthesis Of Daunosamine Research Articles

ChemInform Abstract: Stereocontrolled Routes to cis‐Hydroxyamino Sugars. Part 7. Synthesis of Daunosamine and Ristosamine.

AbstractReaction of the enopyranoside (I) with trichloroacetonitrile yields the imidate (III).

Stereocontrolled routes to cis-hydroxyamino sugars, part VII: synthesis of daunosamine and ristosamine

The nitrogen of an allylic amine can serve as the fulcrum for stereocontrolled delivery of oxygen to an adjacent trigonal site, and cis-hydroxyamino sugars can thus be prepared. Methods for achieving the complementary procedure, namely, control of the delivery of nitrogen to an adjacent site by an allylic oxygen, are described. For example, treatment of methyl 2,3,6-trideoxy-α- l- erythro-hex-2-enopyranoside with trichloroacetonitrile gave an imidate ester which reacted with iodonium dicollidine perchlorate to give 2-trichloromethyl-(methyl 2,3,4,6-tetradeoxy-2-iodo-α- l-altropyranoside)-[3,4- d]-2-oxazoline. Exhaustive reductive dehalogenation of this product followed by hydrolysis led to methyl N-acetyl-α- l-ristosaminide. An analogous series of reactions was used to prepare the corresponding daunosaminide.

ChemInform Abstract: 2,2,5‐Trimethyl‐1,3‐dioxolane‐4‐carboxaldehyde as a Chiral Synthon: Synthesis of the Two Enantiomers of Methyl 2,3,6‐Trideoxy‐α‐L‐threo‐ hex‐2‐enopyranoside, Key Intermediate in the Synthesis of Daunosamine and of (+)‐ and (‐)‐Rhodinose.

AbstractDie isomeren Aldehyde (Ia) und (Ib) werden als chirale Hilfsmittel eingesetzt.

ChemInform Abstract: Electrophilic Additions Controlled by Remote Substituents. Total Synthesis of Daunosamine.

ChemInform Abstract: Electrophilic Additions Controlled by Remote Substituents. Total Synthesis of Daunosamine.

2,2,5-Trimethyl-1,3-dioxolane-4-carboxaldehyde as a chiral synthon: synthesis of the two enantiomers of methyl 2,3,6-trideoxy-.alpha.-L-threo-hex-2-enopyranoside, key intermediate in the synthesis of daunosamine, and of (+)- and (-)-rhodinose

2,2,5-Trimethyl-1,3-dioxolane-4-carboxaldehyde as a chiral synthon: synthesis of the two enantiomers of methyl 2,3,6-trideoxy-.alpha.-L-threo-hex-2-enopyranoside, key intermediate in the synthesis of daunosamine, and of (+)- and (-)-rhodinose

A Stereoselective Synthesis of Daunosamine Utilizing Oxazole Derivatives

A Stereoselective Synthesis of Daunosamine Utilizing Oxazole Derivatives

Synthesis of daunosamine

Synthese a partir de L-arabinose, par l'intermediaire de l'anhydro-3,4 didesoxy-2,6 α-L-ribo-hexopyranoside de methyle

Synthesis of daunosamine

The rearrangement of methyl 3-azido-2- S-benzyl-3-deoxy-2-thio-α- D-altropyranoside ( 3) in methanol to give methyl 3-azido-2- S-benzyl-3-deoxy-2-thio-αβ- D-altrofuranoside ( 4a) was catalysed by Amberlite CG-120(H +) resin. Partial benzoylation of 4a gave the 6- O-benzoyl derivative ( 4b), the 5- O-toluene- p-sulphonyl derivative ( 4c) of which was converted into methyl 5,6-anhydro-3-azido-2- S-benzyl-3-deoxy-2-thio-αβ- L-galactofuranoside ( 7) with methanolic sodium methoxide. Reduction of 7 with lithium aluminium hydride gave the 3,6-dideoxy sugar ( 8a) which, with Raney nickel, gave methyl 3-amino-2,3,6-trideoxy-αβ- L- lyxo-hexofuranoside ( 9). Acid hydrolysis of 9 gave 3-amino-2,3,6-trideoxy- L- lyxo-hexose (daunosamine) which is a component of the antibiotic daunomycin.

The synthesis of daunosamine

The synthesis of daunosamine