Abstract
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.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
