Synthesis of a New Stable Conformationally Constrained 2,7-Anhydrosialic Acid Derivative

Liu, Kegang; Zhou, Haibin; Wu, Yonggang; Yao, Zhu‐Jun

doi:10.1021/jo034679b

Cited by 14 publications

(5 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The cyclisation step was initially carried out in methanol with TFA (4 equiv. ), according to reported procedures for the synthesis of sialic analogues bearing a bicyclic acetal, [22] but a complex mixture of compounds was obtained, probably related with monocyclic species. On the contrary, cyclisation with 95 % TFA, in analogy with other bicyclic compounds yet developed by our group, [13c,14a-14b] afforded the desired products 19 and 20 in Ͼ90 % yield and with good purity, and having the hydroxymethyl moiety at C-5 deprotected from the acid-labile TBDMS group.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Glycidol‐ and Sugar‐Derived Bicyclic β‐ and γ/δ‐Amino Acids for Peptidomimetic Design

Danieli¹,

Trabocchi²,

Menchi³

et al. 2005

Eur J Org Chem

View full text Add to dashboard Cite

Constrained bicyclic β‐ and γ/δ‐amino acids using glycidol and sugar derivatives were developed. The synthetic strategies involved epoxide ring opening of a glycidol derivative, and subsequent coupling with sugar‐derived amines, leading to di‐ or trisubstitued bicyclic scaffolds after cyclisation with trifluoroacetic acid. Achievement of β‐ or γ/δ‐amino acids was accomplished by changing the protecting group strategy of the starting materials. Compatibility of the scaffold with solid‐phase peptide synthesis was assessed by preparing model peptidomimetics using acid‐ and base‐labile resins, thus giving a new tool for peptidomimetic design. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of Glycidol‐ and Sugar‐Derived Bicyclic β‐ and γ/δ‐Amino Acids for Peptidomimetic Design

Danieli¹,

Trabocchi²,

Menchi³

et al. 2005

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…Addition of allylmagnesium bromide to more highly substituted substrates occurred with high diastereoselectivity (Scheme 358). 506 This reaction was a key step in the synthesis of a conformationally constrained sialic acid derivative.…”

Section: Mechanism Of Additions Of Allylmagnesium Reagents To the Car...mentioning

confidence: 99%

Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin–Anh and Chelation-Control Models

et al. 2020

View full text Add to dashboard Cite

This review describes the additions of allylmagnesium reagents to carbonyl compounds and to imines, focusing on the differences in reactivity between allylmagnesium halides and other Grignard reagents. In many cases, allylmagnesium reagents either react with low stereoselectivity when other Grignard reagents react with high selectivity, or allylmagnesium reagents react with the opposite stereoselectivity. This review collects hundreds of examples, discusses the origins of stereoselectivities or the lack of stereoselectivity, and evaluates why selectivity may not occur and when it will likely occur. CONTENTS 4.2.5. Additions to β-Substituted Aldehydes 4.2.6. Additions to Aldehydes with Distant Chelating Groups 4.3. Additions to Cyclic Ketones 4.3.1. Alkoxy-Substituted Cyclic Ketones 4.3.2. Additions to Alkoxy-Substituted Five-Membered-Ring Ketones 4.3.3. Additions to Alkoxy-Substituted Four-Membered-Ring Ketones 4.4. Additions of Allylmagnesium Halides to Cyclic Hemiacetals 5. Diastereoselectivity of Reactions of Allylmagnesium Reagents with Carbonyl Compounds by Felkin−Anh Control 5.1. Felkin−Anh Stereoselectivity 5.2. Additions to α-Chiral Acyclic Ketones 5.3. Additions to Chiral Exocyclic Ketones and Aldehydes 5.4. Additions of Allylmagnesium Halides to Chiral Cyclic Ketones Controlled by Felkin−Anh Selectivity 5.5. Additions of Allylmagnesium Halides to Chiral Acyclic Aldehydes 6. Diastereoselectivity of Reactions with Carbonyl Compounds by Steric Approach Control 6.1. Steric Approach Control and Stereoselectivity

show abstract

“…Since 1994, three further synthetic routes for the production of zanamivir have been reported [44,45,46]. Yao and coworkers reported the synthesis of zanamivir using d -glucono-δ-lactone ( 8 ) as the starting material (Scheme 2) [44], which was easily converted into 9 after protection steps and reduction of the carboxylic acid to aldehyde [47,48]. 9 was allowed to react with chiral hydroxylamine 7 , which was prepared from d -mannose, leading to nitrone 10 .…”

Section: Zanamivir Laninamivir and Other Derivativesmentioning

confidence: 99%

Influenza Neuraminidase Inhibitors: Synthetic Approaches, Derivatives and Biological Activity

2016

View full text Add to dashboard Cite

Despite being a common viral disease, influenza has very negative consequences, causing the death of around half a million people each year. A neuraminidase located on the surface of the virus plays an important role in viral reproduction by contributing to the release of viruses from infected host cells. The treatment of influenza is mainly based on the administration of neuraminidase inhibitors. The neuraminidase inhibitors zanamivir, laninamivir, oseltamivir and peramivir have been commercialized and have been demonstrated to be potent influenza viral neuraminidase inhibitors against most influenza strains. In order to create more potent neuraminidase inhibitors and fight against the surge in resistance resulting from naturally-occurring mutations, these anti-influenza drugs have been used as templates for the development of new neuraminidase inhibitors through structure-activity relationship studies. Here, we review the synthetic routes to these commercial drugs, the modifications which have been performed on these structures and the effects of these modifications on their inhibitory activity.

show abstract

Synthesis of a New Stable Conformationally Constrained 2,7-Anhydrosialic Acid Derivative

Abstract: A stereoseletive synthesis of 2,7-anhydrosialic acid derivative 18 was achieved from d-glucono-delta-lactone. A highly syn-selective addition of Grignard reagent to theN-benzylimine 8 served as a key step.

Cited by 14 publications

References 19 publications

Synthesis of Glycidol‐ and Sugar‐Derived Bicyclic β‐ and γ/δ‐Amino Acids for Peptidomimetic Design

Synthesis of Glycidol‐ and Sugar‐Derived Bicyclic β‐ and γ/δ‐Amino Acids for Peptidomimetic Design

Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin–Anh and Chelation-Control Models

Influenza Neuraminidase Inhibitors: Synthetic Approaches, Derivatives and Biological Activity

Contact Info

Product

Resources

About