Synthesis of novel sugar-lactam conjugates using the Aubé reaction

Kurhade, Suresh E.; Mengawade, Tanaji; Bhuniya, Debnath; Palle, Venkata P.; Reddy, D. Srinivasa

doi:10.1039/c0ob00719f

Cited by 8 publications

(5 citation statements)

References 38 publications

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“…The Aubé reaction was performed under similar conditions as the previous work [16]. Cyclohexanone was reacted with azido alcohol (±)- 3 in dichloromethane with varying amounts of BF 3 ·OEt 2 and the results are summarized in Scheme 3 and Table 1.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction

Shinde¹,

Ople²,

Sangtani³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA novel and convenient method utilizing the Aubé reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aubé reaction with various cyclic ketones to give cyclopentenyl-substituted lactams. Upon dihydroxylation, this affords the N-cyclopentenyl-lactam compounds in racemic form. Given the numerous uses of nucleosides and related compounds, we were interested in the synthesis of carbocylic nucleoside mimics. The attempts and results are described herein.

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Section: Resultsmentioning

confidence: 99%

“…Recently, we applied this reaction for the synthesis of sugar–lactam conjugates starting from an azido-alcohol embedded in sugar derivatives and cyclic ketones [16]. In continuation of this work (and also to expand the potential of this chemistry), a new class of compounds were prepared.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction

Shinde¹,

Ople²,

Sangtani³

et al. 2015

Beilstein J. Org. Chem.

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“…For details of the synthesis, see Cheng et al (2011). For related structures, see Sikorski et al (2009), Robertson & Sheldrick (1965), Zhou et al (2002), Kurhade et al(2011). For the iodo derivative, see: Gulab et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

“…Alkyl azidoglycosides such as the title compound (I) are versatile synthetic intermediates for the synthesis of a wide array of biologically important molecules (Cheng et al, 2011;Kurhade et al,2011;Zhou et al,2002).…”

Section: S1 Commentmentioning

confidence: 99%

Methyl 6-azido-6-deoxy-α-D-galactoside

Cheng

Gulab²,

Timmer

et al. 2011

Acta Cryst E

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The structure of the title compound, C7H13N3O5, was solved using data from a multiple fragment crystal. The galactoside ring adopts a 4 C 1 chair conformation. In the crystal, the molecules are linked by strong O—H⋯O hydrogen bonds, which build linkages around the screw axis of the cell in a similar way to the iodo analogue. These C-5 and C-6 packing motifs expand to R 2 2(10), C 2 2(7) and C 2 2 2(8) motifs, as found in closely related compounds.

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“…H NMR (400 MHz, CDCl 3 ): d =1.36 (s, 3 H, acetonide CH 3 ), 1.53 (s, 3 H, acetonide CH 3 ), 3.96 (dd, J = 11.6, 5.2 Hz, 1 H, OCH 2 oxazepine), 4.08 (app. t, J = 10.4, 5.6 Hz, 1 H, C=NCH), 4.29 (d, J = 2.8 Hz, 1 H, glucofuranose H-3), 4.44 (d, J = 12.4 Hz, 1 H, OCH 2 Ph), 4.62 (d, J = 11.6 Hz, 1 H, OCH 2 Ph), 4.67 (d, J = 3.6 Hz, 1 H, glucofuranose H-2), 4.88 (dd, J = 6.0, 2.9 Hz, 1 H, glucofuranose H-4), 5.01 (d, J = 11.6 Hz, 1 H, OCH 2 oxazepine), 6.07 (d, J = 3.6 Hz, 1 H, glucofuranose H-1), 6.20 (s,1 H, oxazepine H-9), 7.10-7.24(m, 5 H), 5 H), 7.68 (d, J = 7.6 Hz, 2 H), 7.74 (d, J = 8.4 Hz, 2 H).…”

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confidence: 99%