Title:
ピロリジン類の製造方法及び中間体化合物
Document Type and Number:
Japanese Patent JP3934047
Kind Code:
B2
Abstract:
Processes for the preparation of pyrrolidones and pyrrolidines from tri-O-acetyl-D- erythro -4-pentulosonic acid esters are described. The compounds are aza sugar analogs of D-ribofuranoside and are intermediates to drugs which regulate nucleoside and nucleic acid synthesis.
Inventors:
Hollingsworth, Raoul, Ai
Application Number:
JP2002516262A
Publication Date:
June 20, 2007
Filing Date:
May 14, 2001
Export Citation:
Assignee:
Michigan State University
International Classes:
C07C67/317; C07C67/39; C07C69/716; C07C249/02; C07C251/08; C07D207/12; C07D207/273; C07H7/02; C07D207/26
Domestic Patent References:
| JP2000095686A | ||||
| JP2172972A | ||||
| JP3127797A | ||||
| JP2196758A | ||||
| JP7504667A | ||||
| JP11255742A | ||||
| JP61171465A |
Foreign References:
| US5461071 | ||||
| US5286877 |
Other References:
The Journal of Organic Chemistry, Vol.50, No.24, pp4980-4982
Moreaux V.他,Sugar Lactams and Lactim Esters, Useful Precursors of Cyclic Amidines, from Intermolecular Nucleophilic Displacements,Sugar Lactams and Lactim Esters, Useful Precursors of Cyclic Amidines, from Intermolecular Nucleophilic Displacements,1997年,Vol 38(26),4655-4658
Nicole L. 他,Regio-and Stereoselective Opening of Oxiranes through Neighbouring Group Participation: Stereocontrolled Synthesis of Enantiopure Hydroxylated Oxazolidin-2-ones,Eur.J.Org.Chem,1999年,3483-3488
Jones W.C.他,Identification of the 2-hydroxymethyl-3,4-dihydroxypyrrolidine( or 1,4-dideoxy-1,4-iminopentitol) from Anglylocalyx Boutiqueanus and from Arachiniodes Standishii as the (2R,3R,4S)-isomer by the Synthesis of Enantiomer,Tetrahedron Letters,1985年,26(26),3125-3126
Fleet G.W.J他,Potent Competitive Inhibition of alpha-galactosidase and alpha-Glucosidase Activity by 1,4-dideoxy-1,4-iminopentitols: Synthesis of 1,4-Dideoxy-1,4-imino-D-Lyxitol and of both Enantiomaers of 1,4-dideoxy-1,4-iminoarabinitol,Tetrahedron Letters,1985年,26(26),3127-3130
Bock K.,他 ,Preparation of 3-Deoxy-aldonolactones by Hydogenolysis of Acetylated Aldonolactones,Acta Chemica Scandinavica,1981年,B35,155-162
Torii, S.他,A facile procedure for oxidative cleavage of enolic olefins to thecarbonyl compounds with ruthenium tetroxide (RuO4),Journal of Organic Chemistry,1985年,50(24),4980-2
Koiso, Y他,The effect of rice plant components on rice plant pathogen. I. Isolation of anastomosis promoting factors for conidia of G. oryzae from a rice plant (1),Yakugaku Zasshi,1986年,106(5),383-90
Boutellier, M他,Design and preparation of D-ribofuranoamidrazones as inhibitors of nucleoside processing enzymes,Synlett,1995年,(Spec. Issue),510-512
Griffart-Brunet, D他 ,A short diastereoselective synthesis of the natural (2R, 3R,4R)-2-hydroxymethyl-3,4-dihydroxypyrrolidine ,Tetrahedron Letters,1994年,35(18),2889-90
Boutellier, M他,Amidrazone Analogs of D-Ribofuranose as Transition-State Inhibitors of Nucleoside Hydrolase ,Biochemistry,1994年,33(13),3994-4000
Ryu, Y,A Practical and Divergent Way to Trihydroxylated Pyrrolidine Derivatives as Potential Glycosidase Inhibitors via Stereoselective Intermolecular cis-Amidoalkylations ,Journal of Organic Chemistry,1995年,60(1),103-8
Huang, Y ,The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. 1. The Polyhydroxylated Pyrrolidines,The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. 1. The Polyhydroxylated Pyrrolidines,1997年,62(2),372-376
Myhre, D他,Ion-exchange paper chromatography ,Journal of Organic Chemistry,1958年,23,1229-30
Isbell, H他 ,Preparation of lower aldonic acids by oxidation of sugars in alkaline solution,J. Research Natl. Bur. Standards,1942年,29(Research Paper No. 1497),227-32
Kim, Y 他,Synthesis of nectrisine and related compounds, and their biological evaluation ,Tetrahedron ,1999年,55(28),8353-8364
Moreaux V.他,Sugar Lactams and Lactim Esters, Useful Precursors of Cyclic Amidines, from Intermolecular Nucleophilic Displacements,Sugar Lactams and Lactim Esters, Useful Precursors of Cyclic Amidines, from Intermolecular Nucleophilic Displacements,1997年,Vol 38(26),4655-4658
Nicole L. 他,Regio-and Stereoselective Opening of Oxiranes through Neighbouring Group Participation: Stereocontrolled Synthesis of Enantiopure Hydroxylated Oxazolidin-2-ones,Eur.J.Org.Chem,1999年,3483-3488
Jones W.C.他,Identification of the 2-hydroxymethyl-3,4-dihydroxypyrrolidine( or 1,4-dideoxy-1,4-iminopentitol) from Anglylocalyx Boutiqueanus and from Arachiniodes Standishii as the (2R,3R,4S)-isomer by the Synthesis of Enantiomer,Tetrahedron Letters,1985年,26(26),3125-3126
Fleet G.W.J他,Potent Competitive Inhibition of alpha-galactosidase and alpha-Glucosidase Activity by 1,4-dideoxy-1,4-iminopentitols: Synthesis of 1,4-Dideoxy-1,4-imino-D-Lyxitol and of both Enantiomaers of 1,4-dideoxy-1,4-iminoarabinitol,Tetrahedron Letters,1985年,26(26),3127-3130
Bock K.,他 ,Preparation of 3-Deoxy-aldonolactones by Hydogenolysis of Acetylated Aldonolactones,Acta Chemica Scandinavica,1981年,B35,155-162
Torii, S.他,A facile procedure for oxidative cleavage of enolic olefins to thecarbonyl compounds with ruthenium tetroxide (RuO4),Journal of Organic Chemistry,1985年,50(24),4980-2
Koiso, Y他,The effect of rice plant components on rice plant pathogen. I. Isolation of anastomosis promoting factors for conidia of G. oryzae from a rice plant (1),Yakugaku Zasshi,1986年,106(5),383-90
Boutellier, M他,Design and preparation of D-ribofuranoamidrazones as inhibitors of nucleoside processing enzymes,Synlett,1995年,(Spec. Issue),510-512
Griffart-Brunet, D他 ,A short diastereoselective synthesis of the natural (2R, 3R,4R)-2-hydroxymethyl-3,4-dihydroxypyrrolidine ,Tetrahedron Letters,1994年,35(18),2889-90
Boutellier, M他,Amidrazone Analogs of D-Ribofuranose as Transition-State Inhibitors of Nucleoside Hydrolase ,Biochemistry,1994年,33(13),3994-4000
Ryu, Y,A Practical and Divergent Way to Trihydroxylated Pyrrolidine Derivatives as Potential Glycosidase Inhibitors via Stereoselective Intermolecular cis-Amidoalkylations ,Journal of Organic Chemistry,1995年,60(1),103-8
Huang, Y ,The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. 1. The Polyhydroxylated Pyrrolidines,The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. 1. The Polyhydroxylated Pyrrolidines,1997年,62(2),372-376
Myhre, D他,Ion-exchange paper chromatography ,Journal of Organic Chemistry,1958年,23,1229-30
Isbell, H他 ,Preparation of lower aldonic acids by oxidation of sugars in alkaline solution,J. Research Natl. Bur. Standards,1942年,29(Research Paper No. 1497),227-32
Kim, Y 他,Synthesis of nectrisine and related compounds, and their biological evaluation ,Tetrahedron ,1999年,55(28),8353-8364
Attorney, Agent or Firm:
Hideto Asamura
Hajime Asamura
Katsunori Ando
Yukihiro Ikeda
Hajime Asamura
Katsunori Ando
Yukihiro Ikeda