Journal article
Regio and stereoselective conversion of Δ4-uronic acids to l-Ido- and d-glucopyranosiduronic acids
Tetrahedron letters, Vol.38(6), pp.923-926
1997
DOI: 10.1016/S0040-4039(96)02514-2
Abstract
Synthesis of
l-ido- and
d-glucopyranosiduronic acids was performed starting from protected
Δ
4-uronic acids
3a-f. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives
6a-d, which were converted to the corresponding epoxides
7a-d in high yields. Direct reduction of these epoxides using borane-tetrahydrofuran complex afforded the
d-glucopyranosiduronic acids
9b-d, while Lewis acid rearrangment through the C-4 keto intermediate
10b-d afforded the
l-idopyranosiduronic acids
11b-d.
Graphic
Details
- Title: Subtitle
- Regio and stereoselective conversion of Δ4-uronic acids to l-Ido- and d-glucopyranosiduronic acids
- Creators
- Hélène G Bazin - University of IowaRobert.J Kerns - University of IowaRobert J Linhardt - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Tetrahedron letters, Vol.38(6), pp.923-926
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/S0040-4039(96)02514-2
- ISSN
- 0040-4039
- eISSN
- 1873-3581
- Language
- English
- Date published
- 1997
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984365877702771
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