Stereocontrolled palladium(0)-catalyzed preparation of unsaturated azidosugars: an easy access to 2- and 4-aminoglycosides

Oliveira, Ronaldo N. de; Cottier, Louis; Sinou, Denis; Srivastava, Rajendra M.

doi:10.1016/j.tet.2005.06.041

Cited by 33 publications

(20 citation statements)

References 63 publications

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“…(92)) [678]. Sodium azide was used as the nucleophile in the preparation of azidosugars [679]. Iridium catalyzed N-allylations of hydrazines [680].…”

Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…(92)) [678]. Sodium azide was used as the nucleophile in the preparation of azidosugars [679]. Iridium catalyzed N-allylations of hydrazines [680].…”

Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…Unsaturated carbohydrates, similar to those described here, have also been reported to undergo Mitsunobu reaction with simple, non-carbohydrate nucleophiles [29–30]. The palladium-catalysed allylic amination reaction on unsaturated pyranose rings was pioneered thirty years ago by Hanna and Baer [19–20], and has more recently been reinvestigated with rather simple nitrogen nucleophiles [30–31]. Carbohydrate amines have been used as nucleophiles in allylic amination by Shing to form valienamine pseudodisaccharides [21].…”

Section: Introductionmentioning

confidence: 72%

“…Some examples of successful reactions do exist, though, for oxygen, nitrogen and sulfur nucleophiles [25–28]. Unsaturated carbohydrates, similar to those described here, have also been reported to undergo Mitsunobu reaction with simple, non-carbohydrate nucleophiles [29–30]. The palladium-catalysed allylic amination reaction on unsaturated pyranose rings was pioneered thirty years ago by Hanna and Baer [19–20], and has more recently been reinvestigated with rather simple nitrogen nucleophiles [30–31].…”

Section: Introductionmentioning

confidence: 82%

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

Cumpstey¹,

Frigell²,

Pershagen³

et al. 2011

Beilstein J. Org. Chem.

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SummaryDiglycose derivatives, consisting of two monosaccharides linked at non-anomeric positions by a bridging nitrogen atom, have been synthesised. Conversion of one of the precursor monosaccharide coupling components into an unsaturated derivative enhances its electrophilicity at the allylic position, facilitating coupling reactions. Mitsunobu coupling between nosylamides and 2,3-unsaturated-4-alcohols gave the 4-amino-pseudodisaccharides with inversion of configuration as single regio- and diastereoisomers. A palladium-catalysed coupling between an amine and a 2,3-unsaturated 4-trichloroacetimidate gave a 2-amino-pseudodisaccharide as the major product, along with other minor products. Derivatisation of the C=C double bond in pseudodisaccharides allowed the formation of Man(N4–6)Glc and Man(N4–6)Man diglycosides. The amine-linked diglycosides were found to show weak glycosidase inhibitory activity.

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“…Towards this goal, a methyl carbonate leaving group was installed on the allylic alcohol by reaction of 17 with methyl chloroformate to form the C -4-carbonate 18 in 70% yield. Exposing carbonate 18 to the Sinou conditions15 (TMSN 3 , (Pd(allyl)Cl) 2 /1,4-bis(diphenylphosphino)-butane) afforded a single regio- and stereoisomeric allylic azide 19 in 75% yield. However, when alcohol 17 was subjected to Mitsunobu conditions using TMS azide as the nucleophile, no desired C -4-azido compound 21 was formed.…”

mentioning

confidence: 99%

A De Novo Approach to the Synthesis of Glycosylated Methymycin Analogues with Structural and Stereochemical Diversity

et al. 2010

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A divergent and highly stereoselective route to eleven glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and post-glycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of α/β-& D/L-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.

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Stereocontrolled palladium(0)-catalyzed preparation of unsaturated azidosugars: an easy access to 2- and 4-aminoglycosides

Cited by 33 publications

References 63 publications

Transition metals in organic synthesis: Highlights for the year 2005

Transition metals in organic synthesis: Highlights for the year 2005

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

A De Novo Approach to the Synthesis of Glycosylated Methymycin Analogues with Structural and Stereochemical Diversity

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