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4-cyano-3-hydroxybutanoyl hydrazines, derivatives and process for the preparation thereof

Patent ·
OSTI ID:873220
 [1];  [2]
  1. Haslett, MI
  2. East Lansing, MI
+ Show Author Affiliations

Novel 4-cyano-3-hydroxybutanoyl hydrazides (10), particularly R-chiral intermediates are described. The intermediates are useful in preparing (R)-3-hydroxy-4-trimethylaminobutyric acid (L-carnitine) and R-4-amino-3-hydroxybutyric acid (GABOB) and chiral chemical intermediates which are medically useful.

Research Organization:
Michigan State University
DOE Contract Number:
FG02-89ER14029
Assignee:
Board of Trustees Operating Michigan State University (East Lansing, MI)
Patent Number(s):
US 6114566
OSTI ID:
873220
Country of Publication:
United States
Language:
English

References (36)

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Tetrahedron report number 195 (R)- and (S)-2,3-0-isopropylideneglyceraldehyde in stereoselective organic synthesis journal January 1986
Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone journal February 1997
Short and practical syntheses of(R)-(−)-carnitine and (R)-(−)-γ-amino-β-hydroxybutyric acid (GABOB) journal January 1993
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A practical asymmetric synthesis of carnitine journal January 1988
Organic Syntheses Hofmann Rearrangement Under Mildly Acidic Conditions Using [I,I-Bis(Trifluoroacetoxy)]Iodobenzene: Cyclobutylamine Hydrochloride from Cyclobutanecarboxamide book April 2003
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Reviews journal January 1991
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Lipid-lowering effect of carnitine in chronically uremic patients treated with maintenance hemodialysis journal July 1980
Bifunctional chiral synthons via biochemical methods. 5. Preparation of (S)-ethyl hydrogen-3-hydroxyglutarate, key intermediate to (R)-4-amino-3-hydroxybutyric acid and L-carnitine. journal January 1984
Theβ-Lactone Route to a Totally Stereoselective Synthesis of Carnitine Derivatives journal July 1996
(-)-β-Pinene as chiral promoter. Stereospecific access to (-)-γ-amino-β()-hydroxybutyric acid (gabob) and ()-carnitine.2 journal January 1985
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Synthesis of a chiral phospholipase-C and D insensitive membrane probe with excimer emission properties journal February 1998

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