k.comCarbohydrate Research 345 (2010) 2328–2333

Contents lists available at ScienceDirect

Carbohydrate Research

journal h omepage: www.else vier.com/loc ate/carres

Synthesis of seleno-carbohydrates derived from D-galactose

Hugo C. Braga, Ana D. Wouters, Felipe B. Zerillo, Diogo S. Lüdtke ⇑

Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, USP, CEP, 05508-900 São Paulo, SP, Brazil

a r t i c l e i n f o

Article history: Received 23 July 2010 Received in revised form 26 August 2010 Accepted 29 August 2010 Available online 21 September 2010

Keywords: Galactopyranosides Selenium Seleno-carbohydrates …ver más…

In connection with our recent interest in the chemistry of car- bohydrate derivatives,38–41 we decided to expand the scope of our previous work to the synthesis of galactopyranoside deriva- tives containing a selenium moiety in their structures. Keeping in mind the importance of the synthesis of small libraries of com- pounds with different structural motifs for biological screening, the work described herein provides a useful extension of our meth- odology to substrates with a different, more hindered, carbohy- drate scaffold (Fig. 1).42

2. Results and discussion

Initially, the synthesis of an appropriate precursor for the intro- duction of the selenium atom was needed. This was conveniently

0008-6215/$ - see front matter © 2010 Elsevier Ltd. All rights reserved. doi:10.1016/j.carres.2010.08.019

ref . 38 this work

HO O HO OH OH D-xylose HO OH

HO

O

OH OH

PhSe Se OH OH O O

Me O Se
D-galactose

Me O

SeR1

O Me O 1 Me 2

O Me O
2 Me
Me