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2 article(s) from Kandziora, Maja

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

Maja Kandziora and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

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Scheme 1: Approach to divalent carbohydrate mimetics 1 with rigid spacer and monovalent analogues 2.

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Scheme 2: Synthesis of (Z)-nitrone 6. Conditions: a) LiAlH₄, THF, 1 h, rt; b) 1. NaIO₄, CH₃CN/H₂O, 1 h, rt; 2...

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Scheme 3: [3 + 3]-Cyclization of (Z)-nitrone 6 with lithiated allene 9. Conditions: a) n-BuLi, THF, 15 min, −...

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Scheme 4: Synthesis of 1,2-oxazine 4 by acetal formation from 10. Conditions: a) 1-bromo-4-(dimethoxymethyl)b...

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Scheme 5: Synthesis of bicyclic ketone 11 by Lewis acid-induced rearrangement and reduction to alcohols 12a a...

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Scheme 6: Synthesis of bicyclic diols 15 and of trityl-protected bicyclic 1,2-oxazine 16. Conditions: a) SnCl₄...

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Scheme 7: Hydrogenolyses of bicyclic 1,2-oxazine derivatives 15a and 15b. Conditions: a) H₂, Pd/C, MeOH, EtOA...

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Scheme 8: Suzuki cross-coupling of 15a leading to biphenyl derivative 18 and hydrogenolysis to 19. Conditions...

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Scheme 9: Synthesis of N-benzylated p-terphenyl derivative 21 by Suzuki cross-coupling of 12a with 20 and sub...

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Scheme 10: Attempted reductive cleavage of the N–O bond of compound 21 by samarium diiodide and reaction of 12a...

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Scheme 11: Deprotection of compound 21 and samarium diiodide-mediated reaction of 26. Conditions: a) TBAF, THF...

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Scheme 12: Suzuki cross-coupling of compound 16. Conditions: Pd(PPh₃)₂Cl₂, 2 M Na₂CO₃, DMF, 80 °C, 3 d.

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Scheme 13: Hydrogenolysis of compound 27 and samarium diiodide-mediated reaction leading to compounds 30 and 31...

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Published 30 Jul 2014

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Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Léa Bouché,
Maja Kandziora and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 213–223, doi:10.3762/bjoc.10.17

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Scheme 1: General approach to enantiopure the poly(hydroxy)aminopyrans D (n = 0) and the aminooxepanes D (n =...

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Scheme 2: Synthesis of (Z)-nitrone 3. Conditions: a) 1. p-Bromobenzaldehyde dimethylacetal, TFA, DMF, rt, 5 d...

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Scheme 3: Synthesis of 1,2-oxazines syn-7, syn-9 and syn-10. Conditions: a) n-BuLi, THF, −40 °C, 15 min; b) 1...

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Figure 1: Proposed transition structure for the addition of lithiated TMSE-allene 5 to chiral nitrones 3, 6 a...

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Scheme 4: Synthesis of ketones 11, 12 and 13 with a bicyclic 1,2-oxazine skeleton by Lewis acid-induced rearr...

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Scheme 5: Proposed extended chair-like conformation with Zimmerman–Traxler-type transition state.

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Figure 2: GOESY–NMR spectrum (CDCl₃, 500 MHz) of bicyclic 1,2-oxazine 13: irradiation of the 2-H proton. [GOE...

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Scheme 6: Synthesis of triols 14, 15 and 16 by reduction of the carbonyl group and deprotection. Conditions: ...

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Scheme 7: Synthesis of propargylic ether 18. Conditions: a) propargyl bromide, NaOH, TBAI, H₂O/CH₂Cl₂, −20 °C...

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Scheme 8: Synthesis of tricyclic compound 20, bicyclic azide 24 and bicyclic amine 25. Conditions: a) MsCl, Et...

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Scheme 9: Hydrogenolyses of bicyclic and tricyclic 1,2-oxazines 14, 15 and 20 to aminooxepanes 26, 27 and 28....

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Figure 3: Proposed structures of the observed side products 29 and 30 during the hydrogenolyses of 14 and 15.

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Scheme 10: Hydrogenolyses of bicyclic 1,2-oxazines to aminooxepanes 26, 31 and 32 and to diaminooxepane 33 und...

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Published 20 Jan 2014

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