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Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-L-bulgecinine from D-glucuronolactone and of L-DNJ, L-DMDP, and (3S)-3-hydroxy-D-bulgecinine from L-glucuronolactone. DMDP inhibits beta-glucosidases and beta-galactosidases whereas L-DMDP is a potent and specific inhibitor of alpha-glucosidases

Abstract:

A convenient large-scale synthesis of 1-deoxynojirimyin (DNJ) from d-glucuronolactone involves introduction of azide at C-5 with retention of configuration to give 5-azido-5-deoxy-1,2-O-isopropylidene-α-d-glucofuranose as a key intermediate in an overall yield of up to 72%; the same intermediate can be transformed into DMDP [(2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol] and (3R)-3-hydroxy-l-bulgecinine [(2S,3R,4R,5R)-3,4-dihydroxy-5-hydroxymethyl-l-proline]. l-Glucuronolactone, a ...

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Publication status:
Published

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Authors


Weymouth-Wilson, AC More by this author
Clarkson, RA More by this author
Wilson, FX More by this author
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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
21
Issue:
3
Pages:
311-319
Publication date:
2010-03-01
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
URN:
uuid:4f16d765-ebb3-4e31-97d0-7101b86b4c08
Source identifiers:
53376
Local pid:
pubs:53376
Language:
English

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