Details
| Original language | English |
|---|---|
| Pages (from-to) | 2729-2732 |
| Number of pages | 4 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 12 |
| Publication status | Published - 23 Dec 1998 |
| Externally published | Yes |
Abstract
KDO (1) is synthesized in five steps, starting from 1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-mannitol (6). The epoxide 6, obtained from D-mannitol (2), reacts with lithiated silyl dithioacetal 7, followed by acylation of the alcoholate, to the carbonate 9. Silicon-induced lactonization affords the lactone 10, which can be converted into NH4-KDO by standard deprotection procedures.
Keywords
- D-Mannitol, KDO, Oxiranes, Silicon, Thioacetals
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, No. 12, 23.12.1998, p. 2729-2732.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - A Silicon-Mediated Synthesis of 3-Deoxy-D-manno-octulosonic Acid (KDO)
AU - Bräuer, Nico
AU - Kirschning, Andreas
AU - Schaumann, Ernst
PY - 1998/12/23
Y1 - 1998/12/23
N2 - KDO (1) is synthesized in five steps, starting from 1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-mannitol (6). The epoxide 6, obtained from D-mannitol (2), reacts with lithiated silyl dithioacetal 7, followed by acylation of the alcoholate, to the carbonate 9. Silicon-induced lactonization affords the lactone 10, which can be converted into NH4-KDO by standard deprotection procedures.
AB - KDO (1) is synthesized in five steps, starting from 1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-mannitol (6). The epoxide 6, obtained from D-mannitol (2), reacts with lithiated silyl dithioacetal 7, followed by acylation of the alcoholate, to the carbonate 9. Silicon-induced lactonization affords the lactone 10, which can be converted into NH4-KDO by standard deprotection procedures.
KW - D-Mannitol
KW - KDO
KW - Oxiranes
KW - Silicon
KW - Thioacetals
UR - http://www.scopus.com/inward/record.url?scp=0041683955&partnerID=8YFLogxK
U2 - 10.1002/(sici)1099-0690(199812)1998:12<2729::aid-ejoc2729>3.0.co;2-f
DO - 10.1002/(sici)1099-0690(199812)1998:12<2729::aid-ejoc2729>3.0.co;2-f
M3 - Article
AN - SCOPUS:0041683955
SP - 2729
EP - 2732
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 12
ER -