Details
| Original language | English |
|---|---|
| Pages (from-to) | 767-769 |
| Number of pages | 3 |
| Journal | Synlett |
| Volume | 1995 |
| Issue number | 7 |
| Publication status | Published - Jul 1995 |
| Externally published | Yes |
Abstract
Direct iodine(III) promoted azide-transfer to 3-deoxyglycals 1-4 is described, leading to azidoglycals 5a,b-7a,b and hex-2-enopyranosyl azides 8a,b as main products. For the synthesis of precursor 1,5-anhydro-2,3,6-trideoxy-L-threo-hex-1-enitol (L-rhodinal) 3 a new high yielding synthetic variant of the literature is presented. The configuration of the new stereogenic center in 7a,b is determined by comparison of coupling constants with azidoglycal 15 which is obtained by a new synthesis employing a variant of the Mitsunobu reaction.
Keywords
- azidoglycal, hypervalent iodine, L-rhodinal, Mitsunobu reaction
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Synlett, Vol. 1995, No. 7, 07.1995, p. 767-769.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Iodine(III)-Promoted azide transfer to 3-deoxyglycals
AU - Kirschning, Andreas
AU - Domann, Silvie
AU - Dräger, Gerald
AU - Rose, Lars
PY - 1995/7
Y1 - 1995/7
N2 - Direct iodine(III) promoted azide-transfer to 3-deoxyglycals 1-4 is described, leading to azidoglycals 5a,b-7a,b and hex-2-enopyranosyl azides 8a,b as main products. For the synthesis of precursor 1,5-anhydro-2,3,6-trideoxy-L-threo-hex-1-enitol (L-rhodinal) 3 a new high yielding synthetic variant of the literature is presented. The configuration of the new stereogenic center in 7a,b is determined by comparison of coupling constants with azidoglycal 15 which is obtained by a new synthesis employing a variant of the Mitsunobu reaction.
AB - Direct iodine(III) promoted azide-transfer to 3-deoxyglycals 1-4 is described, leading to azidoglycals 5a,b-7a,b and hex-2-enopyranosyl azides 8a,b as main products. For the synthesis of precursor 1,5-anhydro-2,3,6-trideoxy-L-threo-hex-1-enitol (L-rhodinal) 3 a new high yielding synthetic variant of the literature is presented. The configuration of the new stereogenic center in 7a,b is determined by comparison of coupling constants with azidoglycal 15 which is obtained by a new synthesis employing a variant of the Mitsunobu reaction.
KW - azidoglycal
KW - hypervalent iodine
KW - L-rhodinal
KW - Mitsunobu reaction
UR - http://www.scopus.com/inward/record.url?scp=0002547011&partnerID=8YFLogxK
U2 - 10.1055/s-1995-5051
DO - 10.1055/s-1995-5051
M3 - Article
AN - SCOPUS:0002547011
VL - 1995
SP - 767
EP - 769
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 7
ER -