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Effective Organotin...
Effective Organotin-Mediated Regioselective Functionalization of Unprotected Carbohydrates
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- Zhou, Yixuan (author)
- Genomics Research Center, Academia Sinica, No. 128 Academia Road, Section 2, Nankang District, Taipei 11529, Taiwan
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- Liao, Kuo-Shiang (author)
- Genomics Research Center, Academia Sinica, No. 128 Academia Road, Section 2, Nankang District, Taipei 11529, Taiwan
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- Chen, Tzu-Yin (author)
- School of Pharmacy, College of Pharmacy, Taipei Medical University, No. 250 Wu-Hsing Street, Taipei City 110, Taiwan
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- Hsieh, Yves S. Y. (author)
- KTH,Glykovetenskap,Genomics Research Center, Academia Sinica, No. 128 Academia Road, Section 2, Nankang District, Taipei 11529, Taiwan;School of Pharmacy, College of Pharmacy, Taipei Medical University, No. 250 Wu-Hsing Street, Taipei City 110, Taiwan
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- Wong, Chi-Huey (author)
- Genomics Research Center, Academia Sinica, No. 128 Academia Road, Section 2, Nankang District, Taipei 11529, Taiwan;Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States
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Genomics Research Center, Academia Sinica, No 128 Academia Road, Section 2, Nankang District, Taipei 11529, Taiwan School of Pharmacy, College of Pharmacy, Taipei Medical University, No. 250 Wu-Hsing Street, Taipei City 110, Taiwan (creator_code:org_t)
- American Chemical Society (ACS), 2023
- 2023
- English.
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In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 88:11, s. 7174-7151
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- Regioselective functionalization of unprotected carbohydrates at a secondary OH group in the presence of primary OH groups based on the commonly used organotin-mediated reaction has been improved. We found that the preactivation of the dibutylstannylene acetal intermediate with tetrabutylammonium bromide in toluene is a key to the improved condition for the efficient, high-yielding, and regioselective tosylation, benzoylation, or benzylation of unprotected carbohydrates. The counteranion of tetrabutylammonium ion with a weak coordination ability plays a crucial role in the improved regioselective reactions. A convenient access to the intermediates of synthetic value is also demonstrated in the organotin-mediated regioselective tosylation of unprotected carbohydrates, followed by the nucleophilic inversion reaction to give sulfur-containing and azide-modified carbohydrates.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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