PMID: 1203904Nov 1, 1975Paper

A preparative synthesis of 3-amino-2,3,6-trideoxy-L-lyxo-hexose (daunosamine) hydrochloride from D-mannose

Carbohydrate Research
Derek Horton, W Weckerle

Abstract

A simple, preparative route in nine steps from methyl alpha-D-mannopyranoside (1) is described that affords, in 40% overall yield, the title amino sugar 11, the sugar constituent of the antitumor antibiotics adriamycin and daunorubicin. The 2,3:4,5-dibenzylidene acetal (2) of 1 is converted by butyllithium into the 2-deoxy-3-ketone 3, whose oxime 4 is reduced with high stereoselectivity to the D-ribo amine, isolated as its N-acetyl derivative 5 and converted by action of N-bromosuccinimide into the 4-O-benzoyl-6-bromide 7. Dehydrohalogenation of gives the 5,6-unsaturated glycoside 8, which, after O-debenzoylation to 9, undergoes stereospecific reduction by hydrogen with net C-5 inversion to give the crystalline, N-acetylated methyl beta-glycoside (10) of daunosamine, readily converted into daunosamine hydrochloride (11) and into the crystalline N-benzoyl (14) and N-acetyl(15) derivatives. No chromatographic procedures for isolation are required in any of the steps.

References

Aug 1, 1971·European Journal of Cancer : Official Journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR)·G BonadonnaG Beretta

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Citations

Jul 15, 1985·Carbohydrate Research·H H Baer, A Jaworska-Sobiesiak
Sep 20, 2005·Carbohydrate Research·Kathrin Wiedemeyer, Bernhard Wünsch
Sep 1, 1977·Carbohydrate Research·H BellE Winter-Mihaly
Feb 21, 2013·The Journal of Antibiotics·Kei KitamuraKeisuke Suzuki
Aug 11, 2006·Organic Letters·Sebastian A Testero, Rolando A Spanevello
Oct 24, 2007·Carbohydrate Research·Shannon C Timmons, David L Jakeman
Jan 7, 1998·Cell Biochemistry and Function·A ColquhounE A Newsholme
Apr 1, 2010·Chemistry, an Asian Journal·Karl J Hale, Soraya Manaviazar
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May 18, 2000·Organic Letters·S W Baldwin, J S Debenham
Oct 6, 2007·Organic Letters·Anne BodlennerPhilippe Dumas
Nov 8, 2011·The Journal of Organic Chemistry·Yuyong MaBiao Yu
May 9, 2003·Organic Letters·Natasha GemmellHelen M I Osborn
Jun 7, 2003·The Journal of Organic Chemistry·Murray G Rosenberg, Udo H Brinker
May 10, 2007·Chemical Reviews·Odón ArjonaJoaquín Plumet
Oct 7, 2006·Carbohydrate Research·Derek Horton, Anakshi Khare

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