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(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one

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(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one Basic information
Product Name:(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one
Synonyms:(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one;Pachystermine A;20α-dimethylamino-3β-(3'-isopropylidene)-lactam-5α-pregn-4-one;2-Azetidinone, 1-[(3β,5α,20S)-20-(dimethylamino)-4-oxopregnan-3-yl]-3-(1-methylethyl)-, (3R)-
CAS:6156-99-6
MF:C29H48N2O2
MW:456.72
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Mol File:6156-99-6.mol
(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one Structure
(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one Chemical Properties
Melting point 220-4°C
Boiling point 560.7±25.0 °C(Predicted)
density 1.060±0.06 g/cm3(Predicted)
pka9.60±0.50(Predicted)
Safety Information
MSDS Information
(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one Usage And Synthesis
DescriptionThis alkaloid is the major base found in Pachysandra terminalis Sieb. et Zucco Like the other alkaloids present in this plant, it contains the pregnane skeleton. It is dextrorotatory with [α]D + 24° (CHCI 3). It has two keto groups in the molecule, one being present in a four-membered ring. Reduction with NaBH4 furnishes Pachystermine B (q.v.). The structure has been confirmed by the partial synthesis of the alkaloid.
ReferencesKikuchi, Uyeo., Tetrahedron Lett., 3473 (1965)
Kikuchi, Uyeo., Chem. Pharm. Bull., 15, 549 (1967)
Partial synthesis:
Kikuchi et al., Tetrahedron Lett., 909 (1968)
(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one Preparation Products And Raw materials
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