Synthesis Of Hydroxyethylene Dipeptide Isosteres Research Articles

ChemInform Abstract: Stereocontrolled Convergent Synthesis of Hydroxyethylene Dipeptide Isosteres by the Reaction of α-Amino Aldehyde with Alkoxytitanium Homoenolates.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Synthesis of Hydroxyethylene Dipeptide Isosteres That Mimic a Cyclic Amino Acid at the P1′ Subsite.

ChemInform Abstract: Synthesis of Hydroxyethylene Dipeptide Isosteres That Mimic a Cyclic Amino Acid at the P1′ Subsite.

A short approach to the synthesis of the ritonavir and lopinavir core and its C-3 epimer via cross metathesis

A short synthesis of hydroxyethylene dipeptide isostere, a core unit of the HIV-protease inhibitors ritonavir and lopinavir, its C-3 epimer and C 2 symmetric diamino diol is described. The crucial aspects of the synthesis are self-cross metathesis and exploitation of C 2-symmetric of the metathesis product 8 to obtain the required skeleton.

A Stereodivergent Synthesis of Hydroxyethylene Dipeptide Isostere via Highly Diastereoselective Epoxidation

Epoxidation of δ-amino-β,γ-unsaturated ester with tri­fluoroperacetic acid afforded its epoxide in a highly diastereo­selective manner. Subsequent stereodivergent epoxide opening reactions provided synthetic routes towards both the threo and erythro hydroxyethylene peptide isostere.

Epoxyalcohol route to hydroxyethylene dipeptide isosteres. Stereodivergent synthesis of the diamino alcohol core of ritonavir and its C-2 epimer.

A stereoselective synthesis of hydroxyethylene dipeptide isosteres based on the 1,4-diamino-2-hydroxybutane structure is described. Horner-Emmons olefination of phosphonates derived from alpha-amino acids, stereoselective reduction of the resulting enones to allylic alcohols, and syn epoxidation of the latter lead to enantiomerically pure 1-amino-2-hydroxy-3,4-epoxybutanes, key intermediates in the synthesis. Reductive cleavage of the epoxy alcohols with Red-Al proceeds in a highly regioselective way, giving 1-amino-2,4-dihydroxybutanes, from which diamino alcohol hydroxyethylene isosteres are obtained by selective protection of the secondary 2-hydroxy group, via cyclization to 1,3-oxazolidinone, and further elaboration of the 4-hydroxy. Both C-2 epimers of 1,4-diamino-2-hydroxybutanes are accessible by appropriate choice of the conditions for cyclization. The approach is demonstrated by the synthesis of a series of six hydroxyethylene dipeptide isosteres, including the diamino alcohol core of potent HIV-protease inhibitor ritonavir 18 and its C-2 epimer 11a.

Allyltrichlorostannane additions to chiral dipeptide aldehydes

The first examples of successful allylsilane additions to chiral dipeptide aldehydes are described. Treatment of allylsilanes with tin tetrachloride at room temperature affords allyltrichlorostannane intermediates that reacts with dipeptide aldehydes to give 1,2-syn-homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene dipeptide isosteres.

A Stereocontrolled, Convergent Synthesis of Hydroxyethylene Dipeptide Isosteres

A simple, convergent, and stereoselective synthesis of hydroxyethylene dipeptide isosteres 1 and 2 from scalemic α-hydroxy esters has been developed. The method is short (six steps), efficient (≈15−25% overall), and highly diastereoselective (86−94% de) and enantioselective (>95% ee).

ChemInform Abstract: Stereoselective Synthesis of Hydroxyethylene Dipeptide Isostere from Sugar.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Stereoselective Synthesis of Hydroxyethylene Dipeptide Isostere from Sugar

Abstract Regioselective opening of the aziridine ring in the carbohydrate-based precursor led to the stereoselective synthesis of N-Boc-O-benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid methyl ester, the hydroxyethylene dipeptide isostere moiety of potent HIV-1 protease inhibitor.

ChemInform Abstract: A Simple Strategy for the Synthesis of Hydroxyethylene Dipeptide Isostere from D‐Glucose.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: A General Stereocontrolled Synthesis of Hydroxyethylene Dipeptide Isosteres.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A general stereocontrolled synthesis of hydroxyethylene dipeptide isosteres

Hydroxyethylene dipeptide isosteres were synthesized by stereocontrolled hydroboration of homoallylic alcohols derived from syn protected aminoepoxides followed by chemoselective oxidation of the resulting primary alcohols.

A simple strategy for the synthesis of hydroxyethylene dipeptide isostere from D-glucose

A general approach is outlined here for the synthesis of hydroxyethylene dipeptide isostere ( 1) starting from D-glucose which can be employed to introduce any group at P 1 or P 1, positions of such isosteres. A highly stereoselective synthesis of ( 2R,4 S,5S)- N-Boc- O-benzyl-5-amino4-hydroxy-2-methyl-6-phenylhexanoic acid methyl ester ( 2) is accomplished based on this strategy.

An Efficient Stereocontrolled Strategy for the Synthesis of Hydroxyethylene Dipeptide Isosteres

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAn Efficient Stereocontrolled Strategy for the Synthesis of Hydroxyethylene Dipeptide IsosteresTimothy L. Stuk, Anthony R. Haight, David Scarpetti, Michael S. Allen, Jerome A. Menzia, Timothy A. Robbins, Shyamal I. Parekh, Denton C. Langridge, Jien-Heh J. Tien, and Cite this: J. Org. Chem. 1994, 59, 15, 4040–4041Publication Date (Print):July 1, 1994Publication History Published online1 May 2002Published inissue 1 July 1994https://doi.org/10.1021/jo00094a006RIGHTS & PERMISSIONSArticle Views1093Altmetric-Citations39LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (259 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

CrCl 2 mediated allylation of N-protected α-amino aldehydes. A versatile synthesis of polypeptides containing an hydroxyethylene isostere

Differently substituted allylic bromides react with N-protected amino aldehydes to give intermediate products for the synthesis of hydroxyethylene dipeptide isosteres. The low stereoselectivity of this reaction can be improved using aldehydes protected with hindered groups. This reaction can be efficiently applied to oligopetide aldehydes. We describe a protocol, for the preparation of peptides containing an hydroxyethylene isostere, which allows a rapid variations of the aminoacid sequence

A short stereocontrolled synthesis of hydroxyethylene dipeptide isosteres

A stereocontrolled synthesis of protected hydroxyethylene dipeptide isosteres 14 and 16 is described. It provides the 2R,4S,5S epimers required for the preparation of aspartic proteinase inhibitors. The choice of a benzene ring as a precursor to the carboxylic acid function has enabled us to use the readily accessible chiral Grignard reagent 3 which reach with the protected α-amino aldehyde 8 stereoselectively. Kilogram quantities of 16 have been produced by this route in a satisfactory overall yield. The combination of N- and O-protecting groups employed facilitates the incorporation of 14 or 16 into peptide-based enzyme inhibitors

An Efficient Synthesis of Hydroxyethylene Dipeptide Isosteres: The Core Unit of Potent HIV-1 Protease Inhibitors.

An efficient and stereocontrolled synthesis of hydroxyethylene dipeptide isosteres 1 from commercially available, optically pure D-mannose is described. This synthesis represents a practical and enantioselective entry to a range of other dipeptide isosteres, which are not limited to amino acid derived substituents.

Synthesis of hydroxyethylene dipeptide isosteres that mimic a cyclic amino acid at the P1′ subsite

Abstract Addition of a cyclic allylsilane to N-protected α-amino aldehydes in the presence of a Lewis acid affords the corresponding (S)-homoallylic alcohols. Elaboration to the cyclic hydroxyethylene isosteres is described.

Stereocontrolled convergent synthesis of hydroxyethylene dipeptide isosteres by the reaction of α-amino aldehyde with alkoxytitanium homoenolates

The reaction of (S)-α-dibenzylamino aldehydes with dichloroisopropoxytitanium ester homoenolates gave the corresponding γ-aminoalkyl γ-lactones with high erythro selectivity. The same reaction by the use of amide homoenolates also afforded the corresponding 2-amino alcohols with high erythro-selectivity.

Diastereoselective Synthesis of the Hydroxyethylene Dipeptide Isostere of Leu–Val

Abstract The synthesis of hydroxyethylene dipeptide isostere of Leu–Val, a transition-state mimic, is described. The key steps of this synthetic approach are the homogeneous asymmetric hydrogenation of γ-keto esters by BINAP–Ru(II) complex, and the construction of a 2(S)-isopropyl unit.