Regioselective one-pot protection of glucose

Nature Protocols
Cheng-Chung WangShang-Cheng Hung

Abstract

Detailed protocols for the regioselective protection of individual hydroxyls in monosaccharide units are described here. This expedient methodology incorporates up to seven reaction sequences, obviating the necessity to carry out intermittent tedious work-ups and time-consuming purifications. Using this TMSOTf-catalyzed one-pot protocol, the 2,3,4,6-tetra-O-trimethylsilylated hexopyranosides bearing an anomeric group could be transformed into a whole set of differentially protected 2-alcohols, 3-alcohols, 4-alcohols, 6-alcohols and fully protected monosaccharides in high yields. These tailor-made glycosyl donors and acceptors can then be used for stereoselective one-pot glycosylation for oligosaccharide synthesis. The total time for the preparation of a purified protected sugar unit ranges between 1 and 2 d. This process would otherwise take 1-2 weeks.

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Citations

Jun 30, 2011·Organic Letters·K C NicolaouJochen Becker
Sep 8, 2012·Nature Protocols·Marco FiliceJose M Palomo
Sep 7, 2013·Nature Protocols·Madhu Emmadi, Suvarn S Kulkarni
Jun 30, 2009·Current Opinion in Chemical Biology·Marie-Lyn HechtPeter H Seeberger
Nov 17, 2015·The Journal of Organic Chemistry·Varma SaikamRam A Vishwakarma
Dec 17, 2008·The Journal of Pathology·M R Alison, S Islam
Jan 22, 2010·BioEssays : News and Reviews in Molecular, Cellular and Developmental Biology·Emmanuel Derivery, Alexis Gautreau
Dec 2, 2008·Cell·Ian G Macara, Stavroula Mili
Jun 21, 2016·Journal of Natural Products·Chun-Hsu YaoJinq-Chyi Lee
Jul 12, 2013·ACS Chemical Biology·Francesco Berti, Roberto Adamo
Nov 11, 2014·Chemical Communications : Chem Comm·A Abragam JosephCheng-Chung Wang
Dec 1, 2011·Angewandte Chemie·Che-Hsiung HsuChi-Huey Wong
Dec 20, 2008·Chemistry, an Asian Journal·Fa-Chen ChiShang-Cheng Hung
Jun 24, 2010·Chemical Communications : Chem Comm·Laxmansingh T PadiyarShang-Cheng Hung
Jul 22, 2014·Angewandte Chemie·Cheng-Hsiu ChangShang-Cheng Hung
Feb 2, 2017·Beilstein Journal of Organic Chemistry·Serena TraboniAlfonso Iadonisi
Apr 8, 2020·Organic & Biomolecular Chemistry·Chiao Wen ChenKwok-Kong Tony Mong
Sep 17, 2011·Organic & Biomolecular Chemistry·I-Chi LeeShang-Cheng Hung
Nov 2, 2013·Chemical Communications : Chem Comm·A Abragam JosephCheng-Chung Wang
Dec 24, 2008·Chemistry : a European Journal·Pratap S Patil, Shang-Cheng Hung
Dec 7, 2011·Organic & Biomolecular Chemistry·Shang-Cheng HungYong-Qing Zhong
Mar 1, 2013·Organic & Biomolecular Chemistry·Pratap S PatilShang-Cheng Hung
Feb 27, 2021·The Journal of Organic Chemistry·Welday Desta Weldu, Cheng-Chung Wang
Oct 13, 2010·The Journal of Organic Chemistry·Ken-Lien ChangShang-Cheng Hung
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Jun 6, 2018·Chemical Reviews·Suvarn S KulkarniShang-Cheng Hung
Oct 8, 2014·Journal of the American Chemical Society·Yen-Chun KoShang-Cheng Hung
Jul 12, 2011·The Journal of Organic Chemistry·Vikram A Sarpe, Suvarn S Kulkarni

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