- Abstract:
-
The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 45% from d-lyxonolactone, is a potent specific competitive inhibitor...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1021/jo4005487
-
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- Journal:
- The Journal of organic chemistry
- Volume:
- 78
- Issue:
- 15
- Pages:
- 7380-7397
- Publication date:
- 2013-08-05
- DOI:
- EISSN:
-
1520-6904
- ISSN:
-
0022-3263
- URN:
-
uuid:dbbe2635-7179-45ae-95d2-00bc59d0c97a
- Source identifiers:
-
401268
- Local pid:
- pubs:401268
- Copyright date:
- 2013
Journal article
C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat.
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