Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides

An Tai Wu, Pey Jiuann Wu, Wei Zou, Jiun Ly Chir, Yuan Chun Chang, Shuan Yi Tsai, Chao Qi Guo, Wei Shuan Chang, Yu Chi Hsieh

Research output: Contribution to journalArticle

6 Citations (Scopus)

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 languageEnglish
Pages (from-to)2887-2893
Number of pages7
JournalCarbohydrate Research
Volume343
Issue number17
DOIs
Publication statusPublished - 2008 Nov 24

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Sodium Azide
Esterification
Urethane
Alkylation
Amines
Acetates
Substitution reactions
Derivatives

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Wu, A. T., Wu, P. J., Zou, W., Chir, J. L., Chang, Y. C., Tsai, S. Y., ... Hsieh, Y. C. (2008). Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides. Carbohydrate Research, 343(17), 2887-2893. https://doi.org/10.1016/j.carres.2008.08.005
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. / Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides. In: Carbohydrate Research. 2008 ; Vol. 343, No. 17. pp. 2887-2893.
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author = "Wu, {An Tai} and Wu, {Pey Jiuann} and Wei Zou and Chir, {Jiun Ly} and Chang, {Yuan Chun} and Tsai, {Shuan Yi} and Guo, {Chao Qi} and Chang, {Wei Shuan} and Hsieh, {Yu Chi}",
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Wu, AT, Wu, PJ, Zou, W, Chir, JL, Chang, YC, Tsai, SY, Guo, CQ, Chang, WS & Hsieh, YC 2008, 'Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides', Carbohydrate Research, vol. 343, no. 17, pp. 2887-2893. https://doi.org/10.1016/j.carres.2008.08.005

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 journalArticle

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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

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