SYNTHESIS OF SOME NEW SUGAR BASED 3, 3-DISUBSTITUTED MONOCYCLIC Β-LACTAMS BY ASYMMETRIC [2+2] CYCLOADDITION REACTIONS

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JARAHPOUR A.A.; ALVAND P.

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Paper Information

Journal: IRANIAN JOURNAL OF SCIENCE AND TECHNOLOGY TRANSACTION A- SCIENCE Year:2007 | Volume:31 | Issue:A1 Page(s): 17-22

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Title

SYNTHESIS OF SOME NEW SUGAR BASED 3, 3-DISUBSTITUTED MONOCYCLIC Β-LACTAMS BY ASYMMETRIC [2+2] CYCLOADDITION REACTIONS

Author(s)

JARAHPOUR A.A. | ALVAND P. | Issue Writer Certificate

Keywords

2-AZETIDINONEQ3

ASYMMETRIC SYNTHESISQ3

CHIRAL SCHIFF BASESQ3

SUGARQ3

[2+2] CYCLOADDITIONQ3

Abstract

Carbohydrates constitute a class of inexpensive natural products of high chiral content [1], and play a central role in the posttranslational biological selectivity [2]. O-Acyl-protected glycosylamines, particularly the 2, 3, 4, 6-tetra-O-pivaloyl-D-galactopyranosylamine and its acetyl derivative are effective chiral auxiliaries in the Strecker and Ugi syntheses of α-amino acids [3-5]. Glycosylamines are valuable intermediates in the preparation of nucleosides and drugs [6-8]. Carbohydrate-derived auxiliaries utilize an efficient stereoselective potential in a number of nucleophilic addition reactions on prochiral imines, a- Amino acids, and b-amino acids, and their derivatives can be synthesized in few synthetic steps with high enantiomeric purity. A variety of chiral heterocyclic can readily be obtained from glycosyl imines by stereoselective transformations [9]. The asymmetric Staudinger reaction utilizing 2, 3, 4, 6-tetra-O-acetyl- b-D-galactopyranosylamine or 2, 3, 4, 6-tetra-O-acetyl-b-D-glucopyranosylamine as the chiral auxiliary in the synthesis of 2-AZETIDINONEs has been reported by the authors [10] and others [11]. 2-AZETIDINONE nucleus has been recognized as the central motif of the so-called b-lactam antibiotics, the most widely employed family of antimicrobial agents to date [12]. The importance of b-lactams as synthetic intermediates has been widely recognized in organic synthesis. b-lactam molecules with a quaternary carbon center have been used as building blocks for biologically active compounds [13].

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APA: Copy

JARAHPOUR, A.A., & ALVAND, P.. (2007). SYNTHESIS OF SOME NEW SUGAR BASED 3, 3-DISUBSTITUTED MONOCYCLIC Β-LACTAMS BY ASYMMETRIC [2+2] CYCLOADDITION REACTIONS. IRANIAN JOURNAL OF SCIENCE AND TECHNOLOGY TRANSACTION A- SCIENCE, 31(A1), 17-22. SID. https://sid.ir/paper/117977/en

Vancouver: Copy

JARAHPOUR A.A., ALVAND P.. SYNTHESIS OF SOME NEW SUGAR BASED 3, 3-DISUBSTITUTED MONOCYCLIC Β-LACTAMS BY ASYMMETRIC [2+2] CYCLOADDITION REACTIONS. IRANIAN JOURNAL OF SCIENCE AND TECHNOLOGY TRANSACTION A- SCIENCE[Internet]. 2007;31(A1):17-22. Available from: https://sid.ir/paper/117977/en

IEEE: Copy

A.A. JARAHPOUR, and P. ALVAND, “SYNTHESIS OF SOME NEW SUGAR BASED 3, 3-DISUBSTITUTED MONOCYCLIC Β-LACTAMS BY ASYMMETRIC [2+2] CYCLOADDITION REACTIONS,” IRANIAN JOURNAL OF SCIENCE AND TECHNOLOGY TRANSACTION A- SCIENCE, vol. 31, no. A1, pp. 17–22, 2007, [Online]. Available: https://sid.ir/paper/117977/en

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