RU2004105794A - METHOD FOR PRODUCING AN ANTIBIOTIC OF CARMINOMYCIN OR ITS HYDROCHLORIDE - Google Patents

METHOD FOR PRODUCING AN ANTIBIOTIC OF CARMINOMYCIN OR ITS HYDROCHLORIDE Download PDF

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RU2004105794A
RU2004105794A RU2004105794/04A RU2004105794A RU2004105794A RU 2004105794 A RU2004105794 A RU 2004105794A RU 2004105794/04 A RU2004105794/04 A RU 2004105794/04A RU 2004105794 A RU2004105794 A RU 2004105794A RU 2004105794 A RU2004105794 A RU 2004105794A
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Russia
Prior art keywords
dioxane
methylene chloride
trifluoroacetyl
carminomycin
carried out
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RU2004105794/04A
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Russian (ru)
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RU2260011C1 (en
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Евгени Николаевна Олсуфьева (RU)
Евгения Николаевна ОЛСУФЬЕВА
шова Анна Николаевна Тев (RU)
Анна Николаевна Тевяшова
Мари Николаевна Преображенска (RU)
Мария Николаевна ПРЕОБРАЖЕНСКАЯ
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Евгени Николаевна Олсуфьева (RU)
Евгения Николаевна ОЛСУФЬЕВА
шова Анна Николаевна Тев (RU)
Анна Николаевна Тевяшова
Мари Николаевна Преображенска (RU)
Мария Николаевна ПРЕОБРАЖЕНСКАЯ
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Priority to RU2004105794/04A priority Critical patent/RU2260011C1/en
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (5)

1. Способ получения карминомицина и его гидрохлорида, включающий гликозилирование карминомицинона гликозил-донором 1-,4-O-,3-N-тризамещенным даунозамином в присутствии катализатора в смеси безводных апротонных органических растворителей, удаление блокирующих групп и выделение карминомицина в виде основания или гидрохлорида, отличающийся тем, что в качестве катализатора используется триметилсилилтрифторметансульфонат, в качестве гликозил-донора используется 1,4-ди-O-замещенный-3-N-ацилдаунозамин (2,3,6-тридезокси-3-амино-L-ликсо-гексапираноза),1. A method of obtaining carminomycin and its hydrochloride, comprising glycosylating a carminomycin with a glycosyl donor 1-, 4-O-, 3-N-trisubstituted daunosamine in the presence of a catalyst in a mixture of anhydrous aprotic organic solvents, removing blocking groups and isolating carminomycin in the form of a base or hydrochloride characterized in that trimethylsilyl trifluoromethanesulfonate is used as a catalyst, 1,4-di-O-substituted-3-N-acyldaunosamine (2,3,6-tridesoxy-3-amino-L-lyxo-hexapyranose is used as a glycosyl donor )
Figure 00000001
Figure 00000001
 где R1= трифторацетил или N-(9-Н-флуорен-2-илметокси)карбонил или аллилоксикарбонил, преимущественно N-(9-Н-флуорен-2-илметокси)карбонил или трифторацетил, R2= ацетил или трифторацетил или 4-нитробензоил или аллилоксикарбонил, преимущественно ацетил, R3=трихлорацетамидил или триалкилсилил или ацетил или трифторацетил или 4-нитробензоил или аллилоксикарбонил, преимущественно ацетил, в качестве безводных апротонных органических растворителей используют диоксан - метиленхлорид или диоксан - хлороформ или диоксан - метиленхлорид - диэтиловый эфир или диоксан - ацетон или диоксан - хлороформ - диэтиловый эфир или диоксан - тетрагидрофуран -метиленхлорид или тетрагидрофуран - метиленхлорид или ацетон - метиленхлорид, преимущественно диоксан - метиленхлорид, при этом реакция проводится в присутствии молекулярных сит (преимущественно 4A), удаление блокирующих групп проводят щелочным агентом.where R 1 = trifluoroacetyl or N- (9-H-fluoren-2-ylmethoxy) carbonyl or allyloxycarbonyl, mainly N- (9-H-fluoren-2-ylmethoxy) carbonyl or trifluoroacetyl, R 2 = acetyl or trifluoroacetyl or 4- nitrobenzoyl or allyloxycarbonyl, preferably acetyl, R 3 = trichloroacetamide or a trialkylsilyl or acetyl or trifluoroacetyl or 4-nitrobenzoyl, or allyloxycarbonyl, preferably acetyl, in an anhydrous aprotic organic solvents are dioxane - methylene chloride or dioxane - chloroform or dioxane - methylene chloride - diethyl e ir or dioxane — acetone or dioxane — chloroform — diethyl ether or dioxane — tetrahydrofuran — methylene chloride or tetrahydrofuran — methylene chloride or acetone — methylene chloride, predominantly dioxane — methylene chloride, the reaction being carried out in the presence of molecular sieves (mainly 4A), blocking groups are removed by alkali agent. 2. Способ по п.1, отличающийся тем, что гликозил-донор используют в виде смеси α и β изомеров или в виде индивидуальных α или β изомеров.2. The method according to claim 1, characterized in that the glycosyl donor is used as a mixture of α and β isomers or as individual α or β isomers. 3. Способ по п.1, отличающийся тем, что реакцию проводят при температуре не выше 10°С.3. The method according to claim 1, characterized in that the reaction is carried out at a temperature not exceeding 10 ° C. 4. Способ по п.1, отличающийся тем, что реакцию проводят в атмосфере осушенного воздуха или осушенного инертного газа.4. The method according to claim 1, characterized in that the reaction is carried out in an atmosphere of dried air or dried inert gas. 5. Способ по п.1, отличающийся тем, что удаление защитных групп проводят в присутствии гидроксидов щелочных металлов в водно-органической среде: вода - метанол или вода - диоксан или вода - тетрагидрофуран или вода - ацетон.5. The method according to claim 1, characterized in that the removal of the protective groups is carried out in the presence of alkali metal hydroxides in an aqueous-organic medium: water — methanol or water — dioxane or water — tetrahydrofuran or water — acetone.
RU2004105794/04A 2004-02-27 2004-02-27 Method for preparing antibiotic carminomycine or its hydrochloride RU2260011C1 (en)

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DE06848583T1 (en) * 2005-12-13 2011-03-17 Solux Corporation, San Diego PROCESS FOR THE PREPARATION OF 4-DEMETHYLDAUNORUBICIN
US8846882B2 (en) * 2011-04-29 2014-09-30 Synbias Pharma Ag Method of producing 4-demethoxydaunorubicin

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