Efficient synthesis of the hexasaccharide fragment of landomycin A: using phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.
[carbohydrate structure: see text] The beta-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors.
Yu
Biao
B
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China. byu@pub.sioc.ac.cn
Wang
Ping
P
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000737:chemistry*; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000737:chemistry*
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D006027:Glycosides; D007202:Indicators and Reagents; D009844:Oligosaccharides; D013865:Thioglycosides; C064648:landomycin A