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Synlett

Volumn , Issue 15, 2008, Pages 2321-2325

Synthesis of isofagomine and a new C6 pyrrolidine azasugar with potential biological activity

(4) Espeel, Pieter E R a Piens, Kathleen a Callewaert, Nico a Van Der Eycken, Johan a

a GHENT UNIVERSITY (Belgium)

Author keywords

Asymmetric synthesis; Azasugars; Glycosidase inhibitors; Hydroboration; Ring closing metathesis

Indexed keywords

2,4 BIS(HYDROXYMETHYL) 3 HYDROXYPYRROLIDINE; ALPHA GLUCOSIDASE; ENZYME INHIBITOR; ISOFAGOMINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BIOLOGICAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROBORATION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 53149126482 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078280 Document Type: Article

Times cited : (11)

References (26)

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2
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5
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- D +20 (c = 1, pentane).

6
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7
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- n-hexane-EtOH
- Chiral HPLC analysis
- Chiral HPLC analysis: Chiralcel OD-H; n-hexane-EtOH, 99:1 (isocratic); T = 35°C; UV (λ = 214 nm).
- 1 (isocratic); T = 35°C; UV (λ = 214 nm) , vol.99
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8
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- Incomplete stereoselective epoxidation4 and incomplete regioselective epoxide opening with vinyl cuprate4 both yielded an inseparable mixture of product and starting material
- 4 both yielded an inseparable mixture of product and starting material.

9
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- For a recent related approach towards racemic isofagomine (rac-1), see: Imahori, T.; Ojima, H.; Tateyama, H.; Mihara, Y.; Takahata, H. Tetrahedron Lett. 2008, 49, 265.
- For a recent related approach towards racemic isofagomine (rac-1), see: Imahori, T.; Ojima, H.; Tateyama, H.; Mihara, Y.; Takahata, H. Tetrahedron Lett. 2008, 49, 265.

10
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11
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12
- 53149142718
- Selected Experimental Details: O-Benzylation and Staudinger Reduction of 14: To an ice-cooled solution of 14 (12.17 g, 107.6 mmol, colorless oil) in anhyd DMF (180 mL) was added NaH (6.45 g, 60% dispersion on mineral oil, 161.3 mmol, After stirring for 30 min at 0°C, benzyl bromide (25.6 mL, 214 mmol) was added at 0°C and the reaction was stirred overnight (0°C → r.t, NaOH (60 mL, 2 M aq solution) was added and the mixture was stirred at 80°C during 1 h. The reaction mixture was diluted with H 2O (1 L) and extracted with Et2O (3 x 1 L, The organic phase was washed with brine (1 L) and dried (Na2SO4, The drying agent was filtered and the resulting clear solution was evaporated under reduced pressure. The oil was filtered over silica gel (n-hexane-EtOAc, 9:1) and after evaporation, the crude residue was dissolved in anhyd THF (570 mL, Ph3P (56.4 g, 215.2 mmol) was added and the mixture
- 4: 370.19889; found: 370.19897. Ring-Closing Metathesis of 15

13
- 53149109227
- 2O in 60 min; Phenomenex Luna C18 (2), 5 μ, 250 x 4.6 mm.
- 2O in 60 min; Phenomenex Luna C18 (2), 5 μ, 250 x 4.6 mm.

14
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- RCM can also be accomplished by the Grubbs-Hoveyda catalyst, however, not by the Grubbs first generation catalyst
- RCM can also be accomplished by the Grubbs-Hoveyda catalyst, however, not by the Grubbs first generation catalyst.

15
- 53149138050
- Solutions of Boc-protected 17, 21, 22 and 23 consisted of rotamers complicating interpretation of NMR data.
- Solutions of Boc-protected 17, 21, 22 and 23 consisted of rotamers complicating interpretation of NMR data.

16
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17
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- Freshly prepared (according to the Aldrich Technical Bulletin AL-109) 0.5 M solution of thexylborane in THF.
- (b) Freshly prepared (according to the Aldrich Technical Bulletin AL-109) 0.5 M solution of thexylborane in THF.

18
- 53149116931
- 24: [α]D -4.0 (c, 0.72, H2O, 1H NMR (700 MHz, D2O, δ, 4.09 (app. t, J2,3, J3,4, 8.0 Hz, 1 H, H-3, 3.98 (dd, J2,6a, 3.6 Hz, J6a,6b, 12.6 Hz, 1 H, H-6a, 3.86 (dd, J2,6b, 6.4 Hz, J6a,6b, 12.6 Hz, 1 H, H-6b, 3.82 (dd, J4,7a, 4.6 Hz, J 7a,7b, 11.6 Hz, 1 H, H-7a, 3.73 (dd, J4,7b, 6.3 Hz, J7a,7b, 11.6 Hz, 1 H, H-7b, 3.66 (dd, J 4,5a, 8.7 Hz, J5a,5b, 12.2 Hz, 1 H, H-5a, 3.58 (ddd, J2,6a, 3.6 Hz, J2,6b, 6.4 Hz, J2,3, 8.0 Hz, 1 H, H-2, 3.25 (dd, J4,5b, 9.3 Hz, J5a,5b, 12.2 Hz, 1 H, H-5b, 2.48 (m, 1 H, H-4, 13C NMR (75 MHz, D2O, δ, 70.9 (C-3, 65.3 (C-2, 59.5 C-7, 5
- 3: 148.09681; found: 148.09671.

19
- 53149098829
- When 19 was submitted to the same hydrogenolysis conditions, the TBDMS protecting group remained intact,
- (a) When 19 was submitted to the same hydrogenolysis conditions, the TBDMS protecting group remained intact,

20
- 3042662232
- (b) Ikawa, T.; Sajiki, H.; Hirota, K. Tetrahedron 2004, 60, 6189.
- (2004) Tetrahedron , vol.60 , pp. 6189
- Ikawa, T.¹ Sajiki, H.² Hirota, K.³

21
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- (c) Hattori, K.; Sajiki, H.; Hirota, K. Tetrahedron 2001, 57, 2109.
- (2001) Tetrahedron , vol.57 , pp. 2109
- Hattori, K.¹ Sajiki, H.² Hirota, K.³

22
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- Jespersen, T.¹ Bols, M.² Sierks, M.R.³ Skrydstrup, T.⁴

23
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- 2).
- 2).

24
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- Zhao, H.; Thurkauf, A. Synlett 1999, 1280.
- (1999) Synlett , pp. 1280
- Zhao, H.¹ Thurkauf, A.²

25
- 53149143775
- The inhibition constants (Ki) were determined using four inhibitor concentrations within a limited range around the K i value. Inhibition of β-Glucosidase (Almond, Ki was determined at 37°C using a NaH2PO 4-Na2HPO4 buffer (pH 6.5; 100 mM) and 2-chloro-4-nitrophenyl-β-D-glucoside as substrate. The release of 2-chloro-4-nitrophenol was monitored continuously by measuring absorbance at λ, 405 nm. The Ki values were determined by Dixon plots. Inhibition of α-Glucosidase (Yeast, Ki was determined at 37°C using a NaH2PO4-Na 2HPO4 buffer (pH 5.6; 100 mM) and 4-nitrophenyl-α- D-glucoside as substrate. The release of 4-nitrophenol was monitored by measuring absorbance at λ, 405 nm after addition of 10% Na 2CO3 to sample
- D-mannoside as substrate, and were monitored analogously to the α-glucosidase assay above.

26
- 53149091903
- No significant inhibition of the glycolysis of 4-nitrophenyl-α- D-mannoside was observed at a concentration of 1.9 mM in the presence of 24 or rac-24 (1 mM).
- No significant inhibition of the glycolysis of 4-nitrophenyl-α- D-mannoside was observed at a concentration of 1.9 mM in the presence of 24 or rac-24 (1 mM).

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