Phosphate → [(1S,2S)-2-phenylcyclopropyl]methanol

HRID 1770068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1770068
C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5[CH:36]=[C:35]([C:37](N)=[O:38])[CH2:34][CH:33]=[CH:32]5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.[C:45]([C:53](OC)=O)(=O)[C:46]1C=CC=C[CH:47]=1.P([O-])([O-])([O-])=O.[OH-].[Na+]>C(OCC)C.CCCCCC.CC(O)C>[C:33]1([C@H:34]2[CH2:36][C@@H:35]2[CH2:37][OH:38])[CH:32]=[CH:47][CH:46]=[CH:45][CH:53]=1

Komponenten

8

Edukt 4

HCID 1061PhosphateHCID 14798Sodium HydroxideHCID 84835Methyl phenylglyoxalateHCID 439153Nadh

Produkt 1

HCID 6427564[(1S,2S)-2-phenylcyclopropyl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

A reaction mixture was formed by admixing (i) 50 mg NAD, (ii) 4 ml of 2-propanol and (iii) 5 mmoles of 1-carboxyaldehyde-2-phenylcyclopropane (Example 5), Compound 5, in a liquid medium containing 1 gm of lyophilized PED alcohol dehydrogenase preparation, 75 ml of 50 mM phosphate buffer, pH 7.1, and 25 ml of hexane. The pH of the reaction was maintained constant by addition of 1N NaOH. The reaction mixture was maintained at room temperature until product formation stopped. When product formation stopped, (S,S)-2-phenylcyclo-propylmethanol, Compound 5a, was isolated by removal of the hexane layer and extraction of the aqueous layer with ethyl ether (3×75 ml).

Aufarbeitung

  1. customA reaction mixture was formed
  2. additionin a liquid medium containing

Quellen und Nachweise

ORD-Eintrag
ord-88be013a3b954863836d77ef8bae92e8
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05385833

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