RU2008143847A - METHOD FOR PRODUCING (2RC) -2,5,7,8-TETRAMETHYL-2 - [(4RS, 8RS) -4,8,12-TRIMETHYL TRIDETHYL) -CHROMAN-6-IL-N- (3-OXOLUP-20 (29 ) -EN-28-OIL] -GLICINATE - Google Patents

METHOD FOR PRODUCING (2RC) -2,5,7,8-TETRAMETHYL-2 - [(4RS, 8RS) -4,8,12-TRIMETHYL TRIDETHYL) -CHROMAN-6-IL-N- (3-OXOLUP-20 (29 ) -EN-28-OIL] -GLICINATE Download PDF

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RU2008143847A
RU2008143847A RU2008143847/04A RU2008143847A RU2008143847A RU 2008143847 A RU2008143847 A RU 2008143847A RU 2008143847/04 A RU2008143847/04 A RU 2008143847/04A RU 2008143847 A RU2008143847 A RU 2008143847A RU 2008143847 A RU2008143847 A RU 2008143847A
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glycinate
tocopherol
cbz
dmap
dcc
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RU2008143847/04A
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Russian (ru)
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RU2440366C2 (en
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Усеин Меметович Джемилев (RU)
Усеин Меметович Джемилев
Виктор Николаевич Одиноков (RU)
Виктор Николаевич Одиноков
Анна Юльевна Спивак (RU)
Анна Юльевна Спивак
Оксана Валерьевна Хабибрахманова (RU)
Оксана Валерьевна Хабибрахманова
Резеда Рафисовна Муфаззалова (RU)
Резеда Рафисовна Муфаззалова
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Учреждение Российской академии наук ИНСТИТУТ НЕФТЕХИМИИ И КАТАЛИЗА РАН (RU)
Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран
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Abstract

(2RS)-2,5,7,8-Тетраметил-2-[(4RS,8RS)-4,8,12-триметилтридецил]-хроман-6-ил-N-[3-оксолуп-20(29)-ен-28-оил]-глицината (1), ! ! заключающийся во взаимодействии α-токоферола с N-(бензилоксикарбонил) - глицином (CBz-Gly), активированным N,N'-дициклогексилкарбодиимидом (DCC) и пара(N,N'-диметиламино) пиридином (DMAP) в хлористом метилене при комнатной температуре в течение 2 ч при мольном соотношении: α-токоферол:CBz-Gly:DCC:DMAP, равным 1:(1-1.5):(1-1.5):0.15, с выделением продукта колоночной хроматографией на силикагеле с последующим деблокированием аминогруппы путем гидрогенолиза над палладиевым катализатором в этаноле и вовлечением полученного d,l-α-токоферил-глицината (6) в сочетание с хлорангидридом бетулоновой кислоты при мольном соотношении хлорангидрид бетулоновой кислоты:глицинат альфа-токоферола равным 1:(1-1,5) при комнатной температуре или при кипячении в сухом бензоле или хлористом метилене, или хлороформе в течение 1 ч. (2RS) -2,5,7,8-Tetramethyl-2 - [(4RS, 8RS) -4,8,12-trimethyltridecyl] -chroman-6-yl-N- [3-oxolup-20 (29) - en-28-oyl] glycinate (1),! ! consisting in the interaction of α-tocopherol with N- (benzyloxycarbonyl) - glycine (CBz-Gly), activated with N, N'-dicyclohexylcarbodiimide (DCC) and steam (N, N'-dimethylamino) pyridine (DMAP) in methylene chloride at room temperature for 2 hours at a molar ratio: α-tocopherol: CBz-Gly: DCC: DMAP equal to 1: (1-1.5) :( 1-1.5): 0.15, with product isolation by silica gel column chromatography, followed by the release of the amino group by hydrogenolysis over a palladium catalyst in ethanol and involving the obtained d, l-α-tocopheryl glycinate (6) in combination with chloran betulonic acid hydride at a molar ratio of betulonic acid chloride: alpha-tocopherol glycinate equal to 1: (1-1.5) at room temperature or by boiling in dry benzene or methylene chloride, or chloroform for 1 hour.

Claims (1)

(2RS)-2,5,7,8-Тетраметил-2-[(4RS,8RS)-4,8,12-триметилтридецил]-хроман-6-ил-N-[3-оксолуп-20(29)-ен-28-оил]-глицината (1),(2RS) -2,5,7,8-Tetramethyl-2 - [(4RS, 8RS) -4,8,12-trimethyltridecyl] -chroman-6-yl-N- [3-oxolup-20 (29) - en-28-oyl] glycinate (1),
Figure 00000001
Figure 00000001
 заключающийся во взаимодействии α-токоферола с N-(бензилоксикарбонил) - глицином (CBz-Gly), активированным N,N'-дициклогексилкарбодиимидом (DCC) и пара(N,N'-диметиламино) пиридином (DMAP) в хлористом метилене при комнатной температуре в течение 2 ч при мольном соотношении: α-токоферол:CBz-Gly:DCC:DMAP, равным 1:(1-1.5):(1-1.5):0.15, с выделением продукта колоночной хроматографией на силикагеле с последующим деблокированием аминогруппы путем гидрогенолиза над палладиевым катализатором в этаноле и вовлечением полученного d,l-α-токоферил-глицината (6) в сочетание с хлорангидридом бетулоновой кислоты при мольном соотношении хлорангидрид бетулоновой кислоты:глицинат альфа-токоферола равным 1:(1-1,5) при комнатной температуре или при кипячении в сухом бензоле или хлористом метилене, или хлороформе в течение 1 ч. consisting in the interaction of α-tocopherol with N- (benzyloxycarbonyl) - glycine (CBz-Gly), activated with N, N'-dicyclohexylcarbodiimide (DCC) and steam (N, N'-dimethylamino) pyridine (DMAP) in methylene chloride at room temperature for 2 hours at a molar ratio: α-tocopherol: CBz-Gly: DCC: DMAP equal to 1: (1-1.5) :( 1-1.5): 0.15, with product isolation by silica gel column chromatography, followed by the release of the amino group by hydrogenolysis over a palladium catalyst in ethanol and involving the obtained d, l-α-tocopheryl glycinate (6) in combination with chloran betulonic acid hydride at a molar ratio of betulonic acid chloride: alpha-tocopherol glycinate equal to 1: (1-1.5) at room temperature or by boiling in dry benzene or methylene chloride, or chloroform for 1 hour.
RU2008143847/04A 2008-11-05 2008-11-05 Method of producing (2rs)-2,5,7,8-tetramethyl-2-[(4rs,8rs)-4,8,12-trimethyltridecyl]-chroman-6-yl-n-[3-oxolup-20(29)-en-28-oyl]-glycinate RU2440366C2 (en)

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RU2008143847/04A RU2440366C2 (en) 2008-11-05 2008-11-05 Method of producing (2rs)-2,5,7,8-tetramethyl-2-[(4rs,8rs)-4,8,12-trimethyltridecyl]-chroman-6-yl-n-[3-oxolup-20(29)-en-28-oyl]-glycinate

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10202415B1 (en) 2017-10-19 2019-02-12 King Saud University Method of synthesizing of 3-oxolupenal nanoparticles
CN109674799A (en) * 2019-01-31 2019-04-26 湖南农业大学 Application of the betulinic acid in body lead discharging and preparation lead discharging food, health care product and drug

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10202415B1 (en) 2017-10-19 2019-02-12 King Saud University Method of synthesizing of 3-oxolupenal nanoparticles
CN109674799A (en) * 2019-01-31 2019-04-26 湖南农业大学 Application of the betulinic acid in body lead discharging and preparation lead discharging food, health care product and drug
CN109674799B (en) * 2019-01-31 2020-10-16 湖南农业大学 Application of betulinic acid in body lead elimination and preparation of lead elimination food, health-care product and medicine

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