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A concise synthesis of 2,5-dideoxy-2,5-imino-d-mannitol (DMDP) and HomoDMDP from l-xylose
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Mar2007, Vol. 48 Issue 13, p2369-2372. 4p. - Publication Year :
- 2007
-
Abstract
- Abstract: A short and practical procedure for the preparation of C-2 substituted polyhydroxypyrrolidines is described. The C-2 substituent is introduced by a stereoselective addition of a Grignard reagent to a 2,3,5-protected aldofuranose and the cyclization to the pyrrolidine ring system is performed through a bis-mesylation/double nucleophilic displacement sequence. The efficiency of the methodology was demonstrated by its application to the synthesis of HomoDMDP and DMDP. [Copyright &y& Elsevier]
- Subjects :
- *HYDROXYPYRIDONES
*METHANESULFONATES
*PYRROLIDINE
*RING formation (Chemistry)
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 48
- Issue :
- 13
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24216950
- Full Text :
- https://doi.org/10.1016/j.tetlet.2007.01.125