Ethyl S-4-chloro-3-hydroxybutyrate

Bezeichnung:Ethyl S-4-chloro-3-hydroxybutyrate

CAS-Nr86728-85-0

Englisch Name:Ethyl S-4-chloro-3-hydroxybutyrate

CBNumberCB9448087

SummenformelC6H11ClO3

Molgewicht166.6

MOL-Datei86728-85-0.mol

Ethyl S-4-chloro-3-hydroxybutyrate physikalisch-chemischer Eigenschaften

alpha	-14.5 º (c=neat)
Siedepunkt	93-95 °C5 mm Hg(lit.)
Dichte	1.19 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.453(lit.)
Flammpunkt	109 °C
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
pka	13.23±0.20(Predicted)
Aggregatzustand	Liquid
Farbe	Clear colorless to yellow
Optische Aktivität	[α]23/D 14°, neat
BRN	4657170
InChI	InChI=1S/C6H11ClO3/c1-2-10-6(9)3-5(8)4-7/h5,8H,2-4H2,1H3/t5-/m0/s1
InChIKey	ZAJNMXDBJKCCAT-YFKPBYRVSA-N
SMILES	C(OCC)(=O)C[C@H](O)CCl
CAS Datenbank	86728-85-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	41-22
S-Sätze:	26-36-39
RIDADR	2810
WGK Germany	3
HazardClass	6.1
PackingGroup	III
HS Code	29181990

Gefahreninformationscode (GHS)

Ethyl S-4-chloro-3-hydroxybutyrate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R41:Gefahr ernster Augenschäden.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S39:Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Colorless to light yellow liqui
Verwenden
Ethyl (S)-(?)-4-chloro-3-hydroxybutyrate can be used as a starting material in the synthesis of 4-amino-3-hydroxybutyric acid, a compound of pharmacological importance.
Verwenden
Atorvastatin Intermediate
Biosynthese
Bioreductions catalyzed by alcohol dehydrogenases (ADHs) play an essential role in synthesizing chiral alcohols. A novel ADH, SmADH31, obtained from the Stenotrophomonas maltophilia genome, which can tolerate extremely high concentrations (6 M) of both substrate and product. The coexpression of SmADH31 and glucose dehydrogenase from Bacillus subtilis in Escherichia coli meant that as much as 660 g L–1 (4.0 M) ethyl 4-chloroacetoacetate was completely converted into ethyl (S)-4-chloro-3-hydroxybutyrate [(S)-CHBE] in a monophasic aqueous system with a >99.9% ee value and a high space-time yield (2664 g L–1 d–1). In the 100 ml-scale monophasic aqueous system (in triplicate), 66.0 g COBE (single batch charge) can be completely converted to (S)-CHBE (ee >99.9%) in only 6 h with 2 g of the SmADH31/GDH co-expressing cells. After extraction and evaporation, 61.6 g (S)-CHBE was isolated with 92% yield[1].
Allgemeine Beschreibung
Ethyl (S)-4-chloro-3-hydroxybutanoate is a chiral intermediate generally used to prepare atorvastatin, a cholesterol-lowering drug.
Einzelnachweise
[1] Zeyu Yang. “Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System.” Organic Process Research & Development 24 6 (2020): 1068–1076.

Ethyl S-4-chloro-3-hydroxybutyrate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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