Details
| Original language | English |
|---|---|
| Pages (from-to) | 772-774 |
| Number of pages | 3 |
| Journal | Synlett |
| Volume | 1996 |
| Issue number | 8 |
| Publication status | Published - 1996 |
| Externally published | Yes |
Abstract
Conjugate addition of silyl cuprates 1a,b and lithio trialkyl stannanes 1c,d to monosaccharide-derived 2,3-dihydro-4H-pyran-4-ones 2-5 and 10 constitutes a new entry to silyl- and stannyl glycosides 6-9 and 11-13 which either may be employed for the Sila-Baeyer-Villiger oxidation to give pyranoses or are potential precursors for C-glycosides. The keto functionality in 8a/13a can efficiently be reduced to the alcohol in 14a or methylated to form 15 without affecting the anomeric silyl- or stannyl group.
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Synlett, Vol. 1996, No. 8, 1996, p. 772-774.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Addition of Silyl- and Stannyl Anions to Carbohydrate-Derived 2,3-Dihydro-4H-pyran-4-ones
T2 - Facile Access to Glycosyl Silanes and -Stannanes
AU - Kirschning, Andreas
AU - Harders, Jan
PY - 1996
Y1 - 1996
N2 - Conjugate addition of silyl cuprates 1a,b and lithio trialkyl stannanes 1c,d to monosaccharide-derived 2,3-dihydro-4H-pyran-4-ones 2-5 and 10 constitutes a new entry to silyl- and stannyl glycosides 6-9 and 11-13 which either may be employed for the Sila-Baeyer-Villiger oxidation to give pyranoses or are potential precursors for C-glycosides. The keto functionality in 8a/13a can efficiently be reduced to the alcohol in 14a or methylated to form 15 without affecting the anomeric silyl- or stannyl group.
AB - Conjugate addition of silyl cuprates 1a,b and lithio trialkyl stannanes 1c,d to monosaccharide-derived 2,3-dihydro-4H-pyran-4-ones 2-5 and 10 constitutes a new entry to silyl- and stannyl glycosides 6-9 and 11-13 which either may be employed for the Sila-Baeyer-Villiger oxidation to give pyranoses or are potential precursors for C-glycosides. The keto functionality in 8a/13a can efficiently be reduced to the alcohol in 14a or methylated to form 15 without affecting the anomeric silyl- or stannyl group.
UR - http://www.scopus.com/inward/record.url?scp=0012996706&partnerID=8YFLogxK
U2 - 10.1055/s-1996-5513
DO - 10.1055/s-1996-5513
M3 - Article
AN - SCOPUS:0012996706
VL - 1996
SP - 772
EP - 774
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 8
ER -