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Yokoyama, Masataka; Toyoshima, Hirofumi; Shimizu, Motohiro; Togo, Hideo

doi:10.1039/a604474c

Cited by 37 publications

(19 citation statements)

References 14 publications

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“…[25] The formation of the  isomer 17β was not detected during the cyclization of the 14-(5R) isomer by the same procedure, which occurred in a moderate 39 % yield. Alcohol activation using triflic anhydride or the Mitsunobu [26] procedure does not improve the intramolecular cyclization reaction of this series of compounds.…”

Section: Preparation Of Sugar C-acetylenic Dienophilesmentioning

confidence: 92%

Synthesis of Polyhydroxylated Pyrano‐Pyrrole Derivatives from Carbohydrate Precursors

et al. 2007

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The efficient synthesis of novel polyhydroxy‐tetrahydropyrano‐pyrroles from acetylenic carbohydrate precursors in three to four steps is described. The methodology involves, as key steps, the ring contraction of pyridazine intermediates obtained by an inverse‐demand Diels–Alder reaction and subsequent intramolecular lactonization. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Preparation Of Sugar C-acetylenic Dienophilesmentioning

confidence: 92%

Synthesis of Polyhydroxylated Pyrano‐Pyrrole Derivatives from Carbohydrate Precursors

et al. 2007

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“…[a] = 7.14,2.8 Hz,3.53 (t,2H,J = 7.6 Hz,, 3.81 (s, 3H, OCH 3 ), 3. 3H,2),4.46 (s,2H,OCH 2 ),3H,4,5),6H,7.22 (d,2H,J = 9.0 Hz, ArH).…”

Section: -(4-methoxybenzyloxy)butyn-1-yl-23-o-isopropylidene-5-(4-fmentioning

confidence: 98%

Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide

Sharma

Punna

Hymavathi

et al. 2005

Tetrahedron: Asymmetry

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“…[31] However, reactions between enamine 1 ( Figure 2) and different halogenated derivatives of the required aglycons with use of various P-and As-ligands and different reaction conditions never produced the desired nucleosides. Alternative methods involving the addition of the organometallic derivative of the nucleobases variously to the corresponding lactam 2, [32,33] to the corresponding hemiaminal 3 or to the N-acyliminium ion [34][35][36][37][38] obtained in situ from 3 proved unsuccessful as well.…”

Section: Synthesis Of Phosphoramidite Building Blocksmentioning

confidence: 99%

Pyrrolidino DNA with Bases Corresponding to the 2‐Oxo Deletion Mutants of Thymine and Cytosine: Synthesis and Triplex‐Forming Properties

Mayer

Leumann

2007

Eur J Org Chem

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The dual recognition properties of pyrrolidino DNA species as parallel triplex-forming oligonucleotides were previously found to be strongly dependent upon the nature of the pyrimidine bases. In the structure-activity study presented here we were able to exclude this differential binding being due to their 2-oxo function. We had previously reported on the incorporation of pyrrolidino C-nucleosides into triplex-forming 2Ј-deoxyoligonucleotides (TFOs). The basic nitrogen atom that replaces the 4Ј-oxygen atom of the 2Ј-deoxysugar in such modified units introduces a positive charge in the third strand, and this is able to produce favourable electrostatic interaction with the negatively charged DNA target duplex. A first series of pyrrolidino pseudonucleosides with the bases isocytosine and uracil proved successful for GC base-pair recognition, but was unsuccessful for AT base-pair recognition within the parallel triplex binding motif. Here we report on

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Cited by 37 publications

References 14 publications

Synthesis of Polyhydroxylated Pyrano‐Pyrrole Derivatives from Carbohydrate Precursors

Synthesis of Polyhydroxylated Pyrano‐Pyrrole Derivatives from Carbohydrate Precursors

Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide

Pyrrolidino DNA with Bases Corresponding to the 2‐Oxo Deletion Mutants of Thymine and Cytosine: Synthesis and Triplex‐Forming Properties

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