The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides

Article abstract of DOI:10.1080/07328300008544144

Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO₄, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.

Full text of DOI:10.1080/07328300008544144

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The Role of the C-3 Substituent in
the Asymmetric Dihydroxylation of
Hexo-5-Enofuranosides
Hari Babu Mereyala , P. Mallikarjun Goud , Rajendrakumar
Reddy Gadikota , Rama Krishna Maddala & K. Ramasubba
Reddy
a Organic Chemistry Division III Indian Institute of Chemical
Technology , Hyderabad 500 007, India
b Department of Chemistry, Post Graduate College of
Science, Saifabad , Osmania University , Hyderabad 500 004,
India
c Organic Chemistry Division III Indian Institute of Chemical
Technology , Hyderabad 500 007, India
d Organic Chemistry Division III Indian Institute of Chemical
Technology , Hyderabad 500 007, India
e Department of Chemistry, Post Graduate College of
Science, Saifabad , Osmania University , Hyderabad 500 004,
India
Published online: 27 Feb 2008.
To cite this article: Hari Babu Mereyala , P. Mallikarjun Goud , Rajendrakumar Reddy
Gadikota , Rama Krishna Maddala & K. Ramasubba Reddy (2000) The Role of the C-3
Substituent in the Asymmetric Dihydroxylation of Hexo-5-Enofuranosides, Journal of
Carbohydrate Chemistry, 19:9, 1201-1210, DOI: 10.1080/07328300008544144
To link to this article: http://dx.doi.org/10.1080/07328300008544144
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