Landomycin A hexasaccharide

Roush and Bennett reported the consecutive removal of seven iodine atoms during their synthesis of the landomycin A hexasaccharide unit (46) (equation (25)151. 

This method was applied to the synthesis of the landomycin A hexasaccharide, which contains two p-D-olivose-(1 4)-p-D-olivose disaccharides [26], The 2,3-O- thionocarbonate of the olivosyl donor 30 was activated by MeOTf, leading to the... 

SCHEME 38.48. Synthesis of landomycin A hexasaccharide by Tanaka and Takahashi et al.. 

Roush WR, Bennett CE. A highly stereoselective synthesis of the landomycin A hexasaccharide unit. J. Am. Chem. Soc. 2000 122 6124-6125. 

D-Olivose (2,6-dideoxy-D-arahiKo-hexose, 55D) is part of the glycosidically linked hexasaccharide in Landomycin A (66),144 a member of the angucycline antibiotic family.145... 

Luzhetskyy A, Fedoryshyn M, Durr C et al (2005) Iteratively acting glycosyltransferases involved in the hexasaccharide biosynthesis of landomycin A. Chem Biol 12 725-729... 

In the synthesis of the hexasaccharide fragment of landomycin A, the desirable P-glycosyl linkage of the 2,6-dideoxy unit was successfully formed by use of the TMSOTf-promoted phosphite method (Figure 15) [16]. 

Yu B, Wang R Efficient synthesis of the hexasaccharide fragment of landomycin A using phenyl 2,3-0-thionocarbonyl-1-thioglycosides as 2-deoxy-(3-glycoside precursors. Org. Lett. 2002 4 1919-1922. 

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