Abstract
Iminoalditol analogs of ribopyranosides were prepared by reduction of a vinylogous urethane intermediate formed from methyl 2-C-(5-O-methanesulfonyl-β-d-ribofuranosyl)acetate (1) by treatment with sodium azide in DMF at reflux. The N-alkylated analogs were synthesized either by N-alkylation of the corresponding parent iminoaldithol or, more efficiently, from the product of the reaction of 1 with various alkylamines. The latter process involves an SN2 substitution at C-5 by the amine followed by an intramolecular hetero-Michael reaction under basic conditions. The 'aglycon' of the iminoalditol was also modified through amidation and esterification.
| Original language | English |
|---|---|
| Pages (from-to) | 2887-2893 |
| Number of pages | 7 |
| Journal | Carbohydrate Research |
| Volume | 343 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2008 Nov 24 |
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All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Biochemistry
- Organic Chemistry
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Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides. / Wu, An Tai; Wu, Pey Jiuann; Zou, Wei; Chir, Jiun Ly; Chang, Yuan Chun; Tsai, Shuan Yi; Guo, Chao Qi; Chang, Wei Shuan; Hsieh, Yu Chi.
In: Carbohydrate Research, Vol. 343, No. 17, 24.11.2008, p. 2887-2893.Research output: Contribution to journal › Article
TY - JOUR
T1 - Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides
AU - Wu, An Tai
AU - Wu, Pey Jiuann
AU - Zou, Wei
AU - Chir, Jiun Ly
AU - Chang, Yuan Chun
AU - Tsai, Shuan Yi
AU - Guo, Chao Qi
AU - Chang, Wei Shuan
AU - Hsieh, Yu Chi
PY - 2008/11/24
Y1 - 2008/11/24
N2 - Iminoalditol analogs of ribopyranosides were prepared by reduction of a vinylogous urethane intermediate formed from methyl 2-C-(5-O-methanesulfonyl-β-d-ribofuranosyl)acetate (1) by treatment with sodium azide in DMF at reflux. The N-alkylated analogs were synthesized either by N-alkylation of the corresponding parent iminoaldithol or, more efficiently, from the product of the reaction of 1 with various alkylamines. The latter process involves an SN2 substitution at C-5 by the amine followed by an intramolecular hetero-Michael reaction under basic conditions. The 'aglycon' of the iminoalditol was also modified through amidation and esterification.
AB - Iminoalditol analogs of ribopyranosides were prepared by reduction of a vinylogous urethane intermediate formed from methyl 2-C-(5-O-methanesulfonyl-β-d-ribofuranosyl)acetate (1) by treatment with sodium azide in DMF at reflux. The N-alkylated analogs were synthesized either by N-alkylation of the corresponding parent iminoaldithol or, more efficiently, from the product of the reaction of 1 with various alkylamines. The latter process involves an SN2 substitution at C-5 by the amine followed by an intramolecular hetero-Michael reaction under basic conditions. The 'aglycon' of the iminoalditol was also modified through amidation and esterification.
UR - http://www.scopus.com/inward/record.url?scp=53849101375&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=53849101375&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2008.08.005
DO - 10.1016/j.carres.2008.08.005
M3 - Article
C2 - 18723166
AN - SCOPUS:53849101375
VL - 343
SP - 2887
EP - 2893
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 17
ER -