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Gabriel M. J. Lenagh-Snow,
Sarah F. Jenkinson,
Scott J. Newberry,
Atsushi Kato,
Shinpei Nakagawa,
Isao Adachi,
Mark R. Wormald,
Akihide Yoshihara,
Kenji Morimoto,
Kazuya Akimitsu,
Ken Izumori,
George W. J. Fleet
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ABSTRACT: Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ.
Organic Letters 04/2012; 14(8):2050-2053. · 5.86 Impact Factor
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ABSTRACT: Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.
Organic Letters 04/2012; 14(8):2142–2145. · 5.86 Impact Factor
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[show abstract]
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ABSTRACT: Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.
Organic Letters 04/2012; 14(8):2142-5. · 5.86 Impact Factor
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Gabriel M J Lenagh-Snow,
Sarah F Jenkinson,
Scott J Newberry,
Atsushi Kato,
Shinpei Nakagawa,
Isao Adachi,
Mark R Wormald,
Akihide Yoshihara,
Kenji Morimoto,
Kazuya Akimitsu,
Ken Izumori,
George W J Fleet
[show abstract]
[hide abstract]
ABSTRACT: Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ.
Organic Letters 04/2012; 14(8):2050-3. · 5.86 Impact Factor
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[hide abstract]
ABSTRACT: Efficient ring closure of stable crystalline 3,5-di-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammalian α-glucosidases is shown by L-xylo- and L-arabino-iminosugar azetidines.
Organic Letters 11/2011; 13(21):5834-7. · 5.86 Impact Factor
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ABSTRACT: Efficient ring closure of stable crystalline 3,5-di-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammalian α-glucosidases is shown by l-xylo- and l-arabino-iminosugar azetidines.
Organic Letters 10/2011; 13(21):5834–5837. · 5.86 Impact Factor
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ABSTRACT: The structure determination confirms the stereochemistry of the title compound, C(12)H(17)NO(3), which contains a four-membered azetidine ring system. The absolute configuration was determined by the use of d-glucose as the starting material. In the crystal, O-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules into layers in the ab plane.
Acta Crystallographica Section E Structure Reports Online 09/2011; 67(Pt 9):o2452. · 0.35 Impact Factor
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ABSTRACT: In the title compound, C13H21N3O6, the six-membered ring adopts a twist-boat conformation with the azide group in the bowsprit position. The azide group is disordered over two sets of sites in a 0.642 (10):0.358 (10) ratio. The crystal structure consists of O—H...O hydrogen-bonded trimer units. The absolute configuration was determined from the use of d-mannose as the starting material.
Acta Crystallographica Section E. 01/2010;
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ABSTRACT: In the title compound, C(13)H(21)N(3)O(6), the six-membered ring adopts a twist-boat conformation with the azide group in the bowsprit position. The azide group is disordered over two sets of sites in a 0.642 (10):0.358 (10) ratio. The crystal structure consists of O-H⋯O hydrogen-bonded trimer units. The absolute configuration was determined from the use of d-mannose as the starting material.
Acta Crystallographica Section E Structure Reports Online 01/2010; 66(Pt 3):o525-6. · 0.35 Impact Factor
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[show abstract]
[hide abstract]
ABSTRACT: The structure determination confirms the stereochemistry of the title compound, C(12)H(17)NO(3), which contains a four-membered azetidine ring system. The absolute configuration was determined by the use of D-glucose as the starting material. In the crystal, O-H center dot center dot center dot O and O-H center dot center dot center dot N hydrogen bonds link the molecules into layers in the ab plane.
Acta Crystallographica Section E-Structure Reports Online. 67:O2452-U1345.
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[show abstract]
[hide abstract]
ABSTRACT: In the title compound, C(13)H(21)N(3)O(6), the six-membered ring adopts a twist-boat conformation with the azide group in the bowsprit position. The azide group is disordered over two sets of sites in a 0.642 ( 10): 0.358 ( 10) ratio. The crystal structure consists of O-H center dot center dot center dot O hydrogen-bonded trimer units. The absolute configuration was determined from the use of D-mannose as the starting material.
Acta Crystallographica Section E-Structure Reports Online. 66:O525-U4200.
