Title:
4-ヒドロキシイソロイシン及びその誘導体のジアステレオ異性体及びエナンチオマーの製造方法
Document Type and Number:
Japanese Patent JP2006508168
Kind Code:
A
Abstract:
Diastereoisomers and enantiomers of 4-hydroxyisoleucine and its derivatives (I) are prepared by reducing an isoxazole derivative (II) to (a) produce (I) directly or (b) form a lactone (III), as racemate or enantiomerically enriched mixture, followed by ring opening under basic conditions in a protic or aprotic solvent, and optionally separation of the form required. Diastereoisomers and enantiomers of 4-hydroxyisoleucine and its derivatives of formula (I) are prepared by reducing an isoxazole derivative of formula (II) to (a) produce (I) directly or (b) form a lactone of formula (III), as racemate or enantiomerically enriched mixture, followed by ring opening under basic conditions in a protic or aprotic solvent, and optionally separation of the form required. R1, R2 = H, Ra, CORa (preferably acetyl), COORa, SO2Ra, or NRaRb; Ra, Rb = 1-12C alkyl, optionally substituted 5-8C mono- or poly-cyclic aryl, or aralkyl; R3 = H or Ra; and R4 = Ra. Independent claims are also included for: (1) preparation of (2S,3R,4S)-4-hydroxyisoleucine (Ia) using the method above; and (2) new compounds of formula (IV), (V), (C1), (C2), (E1) and (E2). Provided that one of R1 and R2 is H and the other is other than H.
Inventors:
Charles Mioskowski
Wagner, Alan
Delamo Marine, Sandra
Katara, Sedlik
Best, Jean-Michel
Wagner, Alan
Delamo Marine, Sandra
Katara, Sedlik
Best, Jean-Michel
Application Number:
JP2004558145A
Publication Date:
March 09, 2006
Filing Date:
December 01, 2003
Export Citation:
Assignee:
Saint-Nacional de la Russier Chesantique (Say Ennes Ale S)
Universite Louis Pasteur
Universite Louis Pasteur
International Classes:
C07C22/02; C07C227/32; C07C229/22; C07C239/18; C07D307/66; C07B53/00; C07B61/00
Domestic Patent References:
| JPH06306053A | 1994-11-01 |
Foreign References:
| WO1999054297A1 | 1999-10-28 | |||
| WO2001015689A1 | 2001-03-08 |
Attorney, Agent or Firm:
Kanji Arai
Naotaka Kono
Eiichiro Shimazaki
Naotaka Kono
Eiichiro Shimazaki