Details
| Original language | English |
|---|---|
| Pages (from-to) | 1133-1137 |
| Number of pages | 5 |
| Journal | Synthesis |
| Issue number | 8 |
| Publication status | Published - 31 Dec 2000 |
| Externally published | Yes |
Abstract
The preparation of new tail to tail dimers of bridged aminodeoxysugars 2 and 11 is described. The first key step in the synthesis is the formation of the aminomethyl bridge in the carbohydrate-derived monomer 7 which is achieved by silver promoted ring closure of methyl 3-acetamido-6-bromo-2,3,6- trideoxy α-D-glucoside 6. Secondly, olefin metathesis of the corresponding 4-O-allyl glycoside 9 constitutes a powerful tool for dimerization, which allows synthesis of 1,4-butanediol-linked tail to tail neooligosaccharides 2 and 11.
Keywords
- Aminodeoxysugar, Conformational restriction, Metathesis, Neooligosaccharide
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Synthesis, No. 8, 31.12.2000, p. 1133-1137.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of spacer-linked tail to tail dimers derived from a conformationally rigid aminodeoxysugar by olefin metathesis
AU - Kirschning, Andreas
AU - Chen, Guang Wu
PY - 2000/12/31
Y1 - 2000/12/31
N2 - The preparation of new tail to tail dimers of bridged aminodeoxysugars 2 and 11 is described. The first key step in the synthesis is the formation of the aminomethyl bridge in the carbohydrate-derived monomer 7 which is achieved by silver promoted ring closure of methyl 3-acetamido-6-bromo-2,3,6- trideoxy α-D-glucoside 6. Secondly, olefin metathesis of the corresponding 4-O-allyl glycoside 9 constitutes a powerful tool for dimerization, which allows synthesis of 1,4-butanediol-linked tail to tail neooligosaccharides 2 and 11.
AB - The preparation of new tail to tail dimers of bridged aminodeoxysugars 2 and 11 is described. The first key step in the synthesis is the formation of the aminomethyl bridge in the carbohydrate-derived monomer 7 which is achieved by silver promoted ring closure of methyl 3-acetamido-6-bromo-2,3,6- trideoxy α-D-glucoside 6. Secondly, olefin metathesis of the corresponding 4-O-allyl glycoside 9 constitutes a powerful tool for dimerization, which allows synthesis of 1,4-butanediol-linked tail to tail neooligosaccharides 2 and 11.
KW - Aminodeoxysugar
KW - Conformational restriction
KW - Metathesis
KW - Neooligosaccharide
UR - http://www.scopus.com/inward/record.url?scp=0033910330&partnerID=8YFLogxK
U2 - 10.1055/s-2000-6328
DO - 10.1055/s-2000-6328
M3 - Article
AN - SCOPUS:0033910330
SP - 1133
EP - 1137
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 8
ER -