Synthesis of Mono- and Di-O-β-d-glucopyranoside Conjugates of (E)-Resveratrol

Abstract

Starting from the commercially available natural product (E)-resveratrol (1), the four selectively tert-butyldimethylsilyl (TBS) protected (E)-resveratrols 6-9 were prepared by one reaction. Using 6-9 as glucosyl acceptors and trifluoroacetimidate 11 as glucosyl donor, three bioactive natural glucopyranoside conjugates of (E)-resveratrol 2-4 and one novel compound (5) were efficiently prepared in two steps.

carbohydrates - natural products - glycosides - glyco­sylation - phenols

References

<A NAME="RT13005SS-1">1</A>

Present address: Shanghai Medicilon Inc., 67 Libing Road, Building 5, Zhangjiang High-Tech Park, Shanghai 201203, P. R. of China.

<A NAME="RT13005SS-2">2</A> Pervaiz S. FASEB J.  2003,  17:  1975 

<A NAME="RT13005SS-3">3</A> Wang Y. Catana F. Yang Y. Roderick R. van Breemen RB. J. Agric. Food Chem.  2002,  50:  431 

<A NAME="RT13005SS-4">4</A> Frankel EN. Waterhouse AL. Kinsella JE. Lancet  1993,  341:  1103 

<A NAME="RT13005SS-5">5</A> Jang M. Cai L. Udeani GO. Slowing KV. Thomas CF. Beecher CW. Fong HH. Farnsworth NR. Kinghorn AD. Mehta RG. Moon RC. Pezzuto JM. Science  1997,  275:  218 

<A NAME="RT13005SS-6">6</A> Fontecave M. Lepoivre M. Elleigand E. Gerez C. Guittet O. FEBS Lett.  1998,  421:  277 

<A NAME="RT13005SS-7">7</A> Orsini F. Pelizzoni F. Verotta L. Aburjai T. J. Nat. Prod.  1997,  60:  1082 

<A NAME="RT13005SS-8A">8a</A> Hillis WE. Hasegawa M. Biochem. J.  1962,  83:  503 

<A NAME="RT13005SS-8B">8b</A> Aritomi M. Donnelly DMX. Phytochemistry  1976,  15:  2006 

<A NAME="RT13005SS-8C">8c</A> Hanawa F. Tahara S. Mizutani J. Phytochemistry  1992,  31:  3005 

<A NAME="RT13005SS-8D">8d</A> Aburjai TA. Phytochemistry  2000,  55:  407 

<A NAME="RT13005SS-9A">9a</A> Nonaka G. Minani M. Nishioka I. Chem. Pharm. Bull.  1977,  25:  2300 

<A NAME="RT13005SS-9B">9b</A> Teguo PW. Fauconneau B. Deffieux G. Huguet F. Vercauteren J. Merillon J.-M. J. Nat. Prod.  1998,  61:  655 

<A NAME="RT13005SS-9C">9c</A> Fan W. Tezuka Y. Kadota S. Chem. Pharm. Bull.  2000,  48:  1055 

<A NAME="RT13005SS-10A">10a</A> Hano Y. Goi K. Nomura T. Ueda S. Cell Mol. Life Sci.  1997,  53:  237 

<A NAME="RT13005SS-10B">10b</A> Zhou CX. Kong LD. Ye WC. Cheng CHK. Tan RX. Planta Med.  2001,  67:  158 

<A NAME="RT13005SS-11">11</A> Orsini F. Pelizzoni F. Bellini B. Miglierini G. Carbohydr. Res.  1997,  301:  95 

<A NAME="RT13005SS-12">12</A> Brandolini V. Maietti A. Tedeschi P. Durini E. Vertuani S. Manfredini S. J. Agric. Food Chem.  2002,  50:  7407 

<A NAME="RT13005SS-13">13</A> Learmonth DA. Synth. Commun.  2004,  34:  1565 

<A NAME="RT13005SS-14">14</A> Zhang Z. Yu B. J. Org. Chem.  2003,  68:  6309 

<A NAME="RT13005SS-15">15</A> Yu B. Tao H. J. Org. Chem.  2002,  67:  9099 

<A NAME="RT13005SS-16">16</A> Elias C. Gelpi ME. Cadenas RA. J. Carbohydr. Chem.  1995,  14:  1209