Synthesis of α-azido aldehydes Stereoselective access to a protected lincosamine analogue

Sarda, Pierre; Olesker, Alain; Lukacs, Gabor

doi:10.1016/s0040-4020(97)00240-8

Cited by 3 publications

(4 citation statements)

References 12 publications

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“…Due to the limited stability of epoxides 420, the crude materials were usually treated with sodium azide without further purification or isolation. 262,263 Among others, enantiomerically pure protected idofuranose 421, an intermediate of immunosuppressant myriocin was synthesized in this way. In this case, the sterochemical outcome of the ring-opening depended on the structure of the protecting group of the 6-OH group.…”

Section: Synthesis and Reactions Of A-azido Aldehydesmentioning

confidence: 99%

“…In accordance with the S N 2 mechanism at the b-carbon relative to the chlorine atom, both diastereomers gave the same azide (Scheme 84). 263 2-Chlorooxiranes have also been prepared in a different way. The stereoselective dichlorocarbene C-H insertion to silylated 2-alkanols followed by deprotection resulted in the enantiomerically pure dichloromethyl alcohols 424 with complete retention of the configuration.…”

Section: Synthesis and Reactions Of A-azido Aldehydesmentioning

confidence: 99%

“…Their complete reduction to 2-amino-1-alkanols 437 was accomplished by catalytic hydrogenation in the presence of palladium on charcoal under low pressure (3 bar), 262 LAH 256 or sodium borohydride 261 (Scheme 89) although no solvent or any experimental detail was given in this latter case. Sodium borohydride in alcoholic solvents was reported to lead to the selective reduction of the aldehyde functionality to give 2-azido-1-alkanols 438 in excellent (91-99%) yields (Scheme 89), 263,264 providing further proofs for the higher reactivity of the carbonyl group in the presence of the azido functionality (cf. Chapter 3.1.2.).…”

Section: Synthesis and Reactions Of A-azido Aldehydesmentioning

confidence: 99%

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Syntheses and transformations of α-azido ketones and related derivatives

2011

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Organic azides are known and utilized in the synthetic organic chemistry as amine precursors, potential sources of nitrenes, dipoles useful in 1,3-dipolar cycloadditions and starting materials of phosphoranes for a long time, and their literature has been overviewed by several authors. On the other hand, there are some special subclasses within the azides which possess peculiar and interesting properties differing from those of the majority and offering extra synthetic possibilities. In this critical review we wish to give an exhaustive overview on the synthesis and synthetic potential of α-azido ketones and related systems, an underestimated group of compounds. The enhanced acidity of the α-hydrogen offers various new synthetic applications including the creation of a new C-C bond, while the joint presence of the carbonyl and vinyl functions of α-azido-α,β-unsaturated ketones results in a special reactivity, too. Chemo- and stereoselectivity issues also represent important points which are discussed in detail. Finally, the usefulness of the titled derivatives in the synthesis of various heterocycles is reviewed (273 references).

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Section: Synthesis and Reactions Of A-azido Aldehydesmentioning

confidence: 99%

Section: Synthesis and Reactions Of A-azido Aldehydesmentioning

confidence: 99%

Section: Synthesis and Reactions Of A-azido Aldehydesmentioning

confidence: 99%

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Syntheses and transformations of α-azido ketones and related derivatives

2011

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“…4 During the search for variations of this methodology, we attempted to replace the N-Boc-or N-Fmoc-protected aminoaldehyde with the corresponding R-azidoaldehyde, having in mind to employ the azido group as a surrogate of a protected amine. R-Azidoaldehydes have been very rarely reported in the literature, the only examples being related to sugar chemistry 5 and would be very precious and versatile building blocks in I-MCRs; we, therefore, decided to investigate their synthesis.…”

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Synthesis of 5-Carboxamide-oxazolines with a Passerini−Zhu/Staudinger−Aza−Wittig Two-Step Protocol

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α-Geminal Dihydroxymethyl Piperidine and Pyrrolidine Iminosugars: Synthesis, Conformational Analysis, Glycosidase Inhibitory Activity, and Molecular Docking Studies

et al. 2012

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The Jocic-Reeve and Corey-Link type reaction of dichloromethyllithium with suitably protected 5-keto-hexofuranoses followed by treatment with sodium azide and sodium borohydride reduction gave 5-azido-5-hydroxylmethyl substituted hexofuranoses 7a-c with required geminal dihydroxymethyl group. Removal of protecting groups and converting the C-1 anomeric carbon into free hemiacetal followed by intramolecular reductive aminocyclization with in situ generated C5-amino functionality afforded corresponding 5C-dihydroxymethyl piperidine iminosugars 2a-c. Alternatively, removal of protecting groups in 7b and 7c and chopping of C1-anomeric carbon gave C2-aldehyde that on intramolecular reductive aminocyclization with C5-amino gave 4C-dihydroxymethyl pyrrolidine iminosugars 1b and 1c, respectively. On the basis of the (1)H NMR studies, the conformations of 2a/2b were assigned as (4)C(1) and that of 2c as (1)C(4). The glycosidase inhibitory activities of all five iminosugars were studied with various glycosidase enzymes and compared with natural d-gluco-1-deoxynojirimycin (DNJ). All the five compounds were found to be potent inhibitors of rice α-glucosidase with K(i) and IC(50) values in the nanomolar concentration range. Iminosugars 2b and 1b were found to be more potent inhibitors than their parent iminosugar. These results were substantiated by in silico molecular docking studies.

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Synthesis of α-azido aldehydes Stereoselective access to a protected lincosamine analogue

Cited by 3 publications

References 12 publications

Syntheses and transformations of α-azido ketones and related derivatives

Syntheses and transformations of α-azido ketones and related derivatives

Synthesis of 5-Carboxamide-oxazolines with a Passerini−Zhu/Staudinger−Aza−Wittig Two-Step Protocol

α-Geminal Dihydroxymethyl Piperidine and Pyrrolidine Iminosugars: Synthesis, Conformational Analysis, Glycosidase Inhibitory Activity, and Molecular Docking Studies

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