Literature DB >> 12444630

Synthesis of sialic acids via desymmetrization by ring-closing metathesis.

Eric A Voight1, Christian Rein, Steven D Burke.   

Abstract

Formal total syntheses of the naturally occurring deaminated sialic acids KDN (2), a potential oncofetal antigen, and N-acetylneuraminic acid (Neu5Ac, 1), the most naturally abundant sialic acid, have been accomplished in 46% and 9.3% overall yield, respectively, via a novel ketalization/ring-closing metathesis sequence. The rapid introduction of all oxygen and nitrogen functionality in a completely stereocontrolled manner exploited a rigid 6,8-dioxabicyclo[3.2.1]oct-2-ene template. The 2,7-anhydro-KDN derivative 40 served as an advanced intermediate in each of the two syntheses.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 12444630     DOI： 10.1021/jo0263014

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Practical synthesis of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN).

Authors:  David Crich; Chandrasekhar Navuluri
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  A substrate tagging and two-step enzymatic reaction strategy for large-scale synthesis of 2,7-anhydro-sialic acid.

Authors:  Wanqing Li; Tamashree Ghosh; Yuanyuan Bai; Abhishek Santra; An Xiao; Xi Chen
Journal:  Carbohydr Res       Date:  2019-05-16       Impact factor: 2.104

3.  Two Remarkable Epimerizations Imperative for the Success of an Asymmetric Total Synthesis of (+)-Aigialospirol.

Authors:  Ruth Figueroa; John B Feltenberger; Christle C Guevarra; Richard P Hsung
Journal:  Sci China Chem       Date:  2011-01-01       Impact factor: 9.445

Review 4.  KDN (deaminated neuraminic acid): dreamful past and exciting future of the newest member of the sialic acid family.

Authors:  Sadako Inoue; Ken Kitajima
Journal:  Glycoconj J       Date:  2006-07       Impact factor: 2.916

5.  Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of Medium to Large, P-Stereogenic Bicyclo[n.3.1]phosphates.

Authors:  Soma Maitra; Jana L Markley; Rambabu Chegondi; Paul R Hanson
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

6.  P-Stereogenic Bicyclo[4.3.1]phosphite Boranes: Synthesis and Utility of Tunable P-Tether Systems for the Desymmetrization of C2-Symmetric 1,3-anti-Diols.

Authors:  Jana L Markley; Paul R Hanson
Journal:  Org Lett       Date:  2017-05-04       Impact factor: 6.005

7.  Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.

Authors:  Guillaume Pelletier; Aaron Zwicker; C Liana Allen; Alanna Schepartz; Scott J Miller
Journal:  J Am Chem Soc       Date:  2016-03-01       Impact factor: 15.419

8.  Synthesis of (+)-didemniserinolipid B: application of a 2-allyl-4-fluorophenyl auxiliary for relay ring-closing metathesis.

Authors:  Christopher C Marvin; Eric A Voight; Judy M Suh; Christopher L Paradise; Steven D Burke
Journal:  J Org Chem       Date:  2008-09-24       Impact factor: 4.354

9.  Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C 2-symmetric building block: a strategy for the synthesis of decanolide natural products.

Authors:  Bernd Schmidt; Oliver Kunz
Journal:  Beilstein J Org Chem       Date:  2013-11-18       Impact factor: 2.883
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.