2-O-N-Benzylcarbamoyl as a Protecting Group To Promote β-Selective Glycosylation and Its Applications in the Stereoselective Synthesis of Oligosaccharides.
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| Title: | 2-O-N-Benzylcarbamoyl as a Protecting Group To Promote β-Selective Glycosylation and Its Applications in the Stereoselective Synthesis of Oligosaccharides. |
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| Authors: | Yin-Jen Lu1, Yen-Hsun Lai1, You-Yu Lin1, Yi-Chi Wang1, Pi-Hui Liang1 phliang@ntu.edu.tw |
| Source: | Journal of Organic Chemistry. 4/6/2018, Vol. 83 Issue 7, p3688-3701. 14p. |
| Abstract: | This study examines the utility of the N-benzylcarbamoyl (BnCar) protecting group in glycosylation reactions of the parent O-2 protected carbohydrate donor. It was found that the BnCar group imparted exclusively β-selectivity with primary and secondary alcohols. A mechanistic study revealed the activated intermediate to be the glycosyl triflate in a skew conformation, which results in β-selective glycosylation via an SN2-like pathway. The BnCar group can be readily cleaved using tetrabutylammonium nitrite, without affecting ester and ether protecting groups. Taken together, these results show BnCar to be useful for the synthesis of complex oligosaccharides, an undertaking that requires delicate chemical differentiation of various protecting groups. [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Organic Chemistry is the property of American Chemical Society 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 |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 129019755 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: 2-O-N-Benzylcarbamoyl as a Protecting Group To Promote β-Selective Glycosylation and Its Applications in the Stereoselective Synthesis of Oligosaccharides. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Yin-Jen+Lu%22">Yin-Jen Lu</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Yen-Hsun+Lai%22">Yen-Hsun Lai</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22You-Yu+Lin%22">You-Yu Lin</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Yi-Chi+Wang%22">Yi-Chi Wang</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Pi-Hui+Liang%22">Pi-Hui Liang</searchLink><relatesTo>1</relatesTo><i> phliang@ntu.edu.tw</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 4/6/2018, Vol. 83 Issue 7, p3688-3701. 14p. – Name: Abstract Label: Abstract Group: Ab Data: This study examines the utility of the N-benzylcarbamoyl (BnCar) protecting group in glycosylation reactions of the parent O-2 protected carbohydrate donor. It was found that the BnCar group imparted exclusively β-selectivity with primary and secondary alcohols. A mechanistic study revealed the activated intermediate to be the glycosyl triflate in a skew conformation, which results in β-selective glycosylation via an SN2-like pathway. The BnCar group can be readily cleaved using tetrabutylammonium nitrite, without affecting ester and ether protecting groups. Taken together, these results show BnCar to be useful for the synthesis of complex oligosaccharides, an undertaking that requires delicate chemical differentiation of various protecting groups. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society 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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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1021/acs.joc.8b00047 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 14 StartPage: 3688 Titles: – TitleFull: 2-O-N-Benzylcarbamoyl as a Protecting Group To Promote β-Selective Glycosylation and Its Applications in the Stereoselective Synthesis of Oligosaccharides. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Yin-Jen Lu – PersonEntity: Name: NameFull: Yen-Hsun Lai – PersonEntity: Name: NameFull: You-Yu Lin – PersonEntity: Name: NameFull: Yi-Chi Wang – PersonEntity: Name: NameFull: Pi-Hui Liang IsPartOfRelationships: – BibEntity: Dates: – D: 06 M: 04 Text: 4/6/2018 Type: published Y: 2018 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 83 – Type: issue Value: 7 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
