PL415782A1 - Cis-(4R,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and trans-(4S,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and method for obtaining them simultaneously - Google Patents

Cis-(4R,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and trans-(4S,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and method for obtaining them simultaneously

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Publication number
PL415782A1
PL415782A1 PL415782A PL41578216A PL415782A1 PL 415782 A1 PL415782 A1 PL 415782A1 PL 415782 A PL415782 A PL 415782A PL 41578216 A PL41578216 A PL 41578216A PL 415782 A1 PL415782 A1 PL 415782A1
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PL
Poland
Prior art keywords
dimethylphenyl
dihydrofuran
iodoethane
trans
lactones
Prior art date
Application number
PL415782A
Other languages
Polish (pl)
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PL229558B1 (en
Inventor
Witold Gładkowski
Marcelina Mazur
Aleksandra Jura
Aleksandra Pawlak
Bożena Obmińska-Mrukowicz
Original Assignee
Uniwersytet Przyrodniczy we Wrocławiu
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by Uniwersytet Przyrodniczy we Wrocławiu filed Critical Uniwersytet Przyrodniczy we Wrocławiu
Priority to PL415782A priority Critical patent/PL229558B1/en
Publication of PL415782A1 publication Critical patent/PL415782A1/en
Publication of PL229558B1 publication Critical patent/PL229558B1/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Zgłoszenie dotyczy optycznie czynnych ß-(2',5'-dimetylofenylo)-?-jodo-?-laktonów o wzorach 1 i 2 przedstawionych na rysunku oraz sposobu ich jednoczesnego otrzymywania. Sposób jednoczesnego otrzymywania optycznie czynnych ß-(2',5'-dimetylofenylo)-?-jodo-?-laktonów polega na tym, że (2S,3E)-4-(2',5'-dimetylofenylo)-but-3-en-2-ol przeprowadza się w wyniku trzyetapowej syntezy w mieszaninę jodolaktonów, które następnie wydziela się w postaci czystej metodą chromatografii kolumnowej otrzymując cis-(4R,5R6S)-5-(1-jodoetylo)-4-(2',5'-dimetylofenylo)-dihydrofuran-2-on i trans-(4R,5S,6R)-5-(1-jodoetylo)-4-(2',5'-dimetylofenylo)-dihydrofuran-2-on. Optycznie czynne ß-(2',5'-dimetylofenylo)-?-jodo-?-laktony o wzorach 1 i 2 mogą znaleźć zastosowanie w farmacji, jako związki o działaniu antynowotworowym.The application relates to optically active ß- (2 ', 5'-dimethylphenyl) - α - iodo - α - lactones with formulas 1 and 2 shown in the drawing and the method of their simultaneous preparation. The method of simultaneous preparation of optically active ß- (2 ', 5'-dimethylphenyl) - β - iodo - β-lactones is that (2S, 3E) -4- (2', 5'-dimethylphenyl) -but-3 -en-2-ol is converted as a result of a three-step synthesis to a mixture of iodolactones, which are then isolated in pure form by column chromatography to give cis- (4R, 5R6S) -5- (1-iodoethyl) -4- (2 ', 5 '-dimethylphenyl) -dihydrofuran-2-one and trans- (4R, 5S, 6R) -5- (1-iodoethyl) -4- (2', 5'-dimethylphenyl) dihydrofuran-2-one. Optically active ß- (2 ', 5'-dimethylphenyl) - α - iodo - α - lactones of formulas 1 and 2 may find use in pharmacy as compounds with antitumor activity.

PL415782A 2016-01-13 2016-01-13 Cis-(4R,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and trans-(4S,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and method for obtaining them simultaneously PL229558B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL415782A PL229558B1 (en) 2016-01-13 2016-01-13 Cis-(4R,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and trans-(4S,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and method for obtaining them simultaneously

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL415782A PL229558B1 (en) 2016-01-13 2016-01-13 Cis-(4R,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and trans-(4S,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and method for obtaining them simultaneously

Publications (2)

Publication Number Publication Date
PL415782A1 true PL415782A1 (en) 2017-07-17
PL229558B1 PL229558B1 (en) 2018-07-31

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Family Applications (1)

Application Number Title Priority Date Filing Date
PL415782A PL229558B1 (en) 2016-01-13 2016-01-13 Cis-(4R,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and trans-(4S,5R,6S)-5-(1-iodoethane)-4-(2',5'-dimethylphenyl)dihydrofuran-2-one and method for obtaining them simultaneously

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PL (1) PL229558B1 (en)

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PL229558B1 (en) 2018-07-31

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