Abstract
The Claisen rearrangement of a spiro compound 1 derived from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, with triethyl orthopropionate afforded the rearrangement products 4, 5, and 6 as a 1:2.5:10 diastereomeric mixture. The reaction of 1 with trimethyl orthobutyrate provided a 1:3 mixture of 7 and 8. In both cases, the σ-bond formation proceeded predominantly from the β-side. This stereochemical outcome was opposite to that observed in the case of the rearrangement of 1 with triethyl orthoacetate.
| Original language | English |
|---|---|
| Pages (from-to) | 57-69 |
| Number of pages | 13 |
| Journal | Journal of Carbohydrate Chemistry |
| Volume | 20 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2001 |
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ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Organic Chemistry
Cite this
Orthoester Claisen rearrangement of a D-glucose-derived spirocyclic substrate. / Takao, Kenichi; Saegusa, Hiroshi; Tadano, Kin Ichi.
In: Journal of Carbohydrate Chemistry, Vol. 20, No. 1, 2001, p. 57-69.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Orthoester Claisen rearrangement of a D-glucose-derived spirocyclic substrate
AU - Takao, Kenichi
AU - Saegusa, Hiroshi
AU - Tadano, Kin Ichi
PY - 2001
Y1 - 2001
N2 - The Claisen rearrangement of a spiro compound 1 derived from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, with triethyl orthopropionate afforded the rearrangement products 4, 5, and 6 as a 1:2.5:10 diastereomeric mixture. The reaction of 1 with trimethyl orthobutyrate provided a 1:3 mixture of 7 and 8. In both cases, the σ-bond formation proceeded predominantly from the β-side. This stereochemical outcome was opposite to that observed in the case of the rearrangement of 1 with triethyl orthoacetate.
AB - The Claisen rearrangement of a spiro compound 1 derived from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, with triethyl orthopropionate afforded the rearrangement products 4, 5, and 6 as a 1:2.5:10 diastereomeric mixture. The reaction of 1 with trimethyl orthobutyrate provided a 1:3 mixture of 7 and 8. In both cases, the σ-bond formation proceeded predominantly from the β-side. This stereochemical outcome was opposite to that observed in the case of the rearrangement of 1 with triethyl orthoacetate.
UR - http://www.scopus.com/inward/record.url?scp=0035648222&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035648222&partnerID=8YFLogxK
U2 - 10.1081/CAR-100102543
DO - 10.1081/CAR-100102543
M3 - Article
AN - SCOPUS:0035648222
VL - 20
SP - 57
EP - 69
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
SN - 0732-8303
IS - 1
ER -