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Selective isomerization of a trans-butanediacetal derivative of tartaric acid with differentiating substituents at C-2 and C-3.

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Title: Selective isomerization of a trans-butanediacetal derivative of tartaric acid with differentiating substituents at C-2 and C-3.
Authors: Drop, Adam1, Wojtasek, Hubert1, Frąckowiak-Wojtasek, Bożena1 bozena.frackowiak@uni.opole.pl
Source: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Apr2017, Vol. 58 Issue 15, p1453-1455. 3p.
Subjects: Tartaric acid, Isomerization, Substituents (Chemistry), Thioesters, Chemical derivatives
Abstract: A trans -disubstituted butanediacetal derivative with two different substituents (ester and thioester) – methyl (2 R ,3 R ,5 R ,6 R )-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate, was selectively converted to the cis derivative – methyl (2 S ,3 R ,5 R ,6 R )-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate in high yield on a multigram scale. The product of this reaction offers the possibility for selective modification of one of the substituents, which was demonstrated by Fukuyama reduction of the thioester group. [ABSTRACT FROM AUTHOR]
Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 121972249
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  Data: Selective isomerization of a trans-butanediacetal derivative of tartaric acid with differentiating substituents at C-2 and C-3.
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  Data: <searchLink fieldCode="DE" term="%22Tartaric+acid%22">Tartaric acid</searchLink><br /><searchLink fieldCode="DE" term="%22Isomerization%22">Isomerization</searchLink><br /><searchLink fieldCode="DE" term="%22Substituents+%28Chemistry%29%22">Substituents (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Thioesters%22">Thioesters</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+derivatives%22">Chemical derivatives</searchLink>
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  Data: A trans -disubstituted butanediacetal derivative with two different substituents (ester and thioester) – methyl (2 R ,3 R ,5 R ,6 R )-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate, was selectively converted to the cis derivative – methyl (2 S ,3 R ,5 R ,6 R )-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate in high yield on a multigram scale. The product of this reaction offers the possibility for selective modification of one of the substituents, which was demonstrated by Fukuyama reduction of the thioester group. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.tetlet.2017.02.072
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      – Code: eng
        Text: English
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        Type: general
      – SubjectFull: Isomerization
        Type: general
      – SubjectFull: Substituents (Chemistry)
        Type: general
      – SubjectFull: Thioesters
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      – SubjectFull: Chemical derivatives
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      – TitleFull: Selective isomerization of a trans-butanediacetal derivative of tartaric acid with differentiating substituents at C-2 and C-3.
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              Text: Apr2017
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