Stable axial-rich conformation of pyranoses derived from L-rhamnose and D-mannose

Stable chair conformation with more axial substituents (axial-rich conformation) of pyranoses derived from L-rhamnose and D-mannose is described. The naturally stable ring conformation of L-rhamnose (1C4) and D-mannose (4C1) was flipped by introduction of a TBS group into a hydroxyl group at C-3 and...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 30; pp. 5573 - 5576
Main Authors Yamada, Hidetoshi, Nakatani, Mari, Ikeda, Tomonari, Marumoto, Yuzo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.07.1999
Elsevier
Subjects
carbohydrates
Chemistry
Chemistry, Organic
conformation
Physical Sciences
Science & Technology
carbohydrates
conformation
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Summary:Stable chair conformation with more axial substituents (axial-rich conformation) of pyranoses derived from L-rhamnose and D-mannose is described. The naturally stable ring conformation of L-rhamnose (1C4) and D-mannose (4C1) was flipped by introduction of a TBS group into a hydroxyl group at C-3 and a TPS group into a hydroxyl group at C-4 to give 4C1 and 1C4 conformers, respectively. The naturally stable ring conformation of L-rhamnose (1C4) and D-mannose (4C1) was flipped by introduction of a TPS group into a hydroxyl group at C-3 and a TBS group into a hydroxyl group at C-4 to give 4C1 and 1C4 conformers, respectively.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01077-1