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Cas Database

100009-52-7

100009-52-7

Identification

  • Product Name:3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

  • CAS Number: 100009-52-7

  • EINECS:

  • Molecular Weight:323.392

  • Molecular Formula:C20H21NO3

  • HS Code:

  • Mol File:100009-52-7.mol

Synonyms:

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    Relevant articles and documentsAll total 3 Articles be found

    SYNTHESES OF METHYL N-BENZOYLACOSAMINIDE AND METHYL N-(BENZYLOXYOXALYL)- DAUNOSAMINIDE FROM (S)-ETHYL 3-HYDROXYBUTYRATE

    Ha, Deok-Chan,Hart, David J.

    , p. 4489 - 4492 (2007/10/02)

    A formal total synthesis of acosamine (1) and the preparation of N-acylated daunosamine derivative 4 from a common intermediate (13) is described.

    Preparation of Aminosaccharides Using Ester-Imine Condensations: Syntheses of Methyl N-Benzoylacosaminide and Methyl N-(Oxo(phenylmethoxy)acetyl)daunosaminide from (S)-Ethyl 3-Hydroxybutyrate

    Galluci, Judith C.,Ha, Deok-Chan,Hart, David J.

    , p. 1283 - 1292 (2007/10/02)

    The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl imine 2 to afford β-lactam 4.The same dianion reacted with N-aryl imine 10 to give β-lactams 11, 12, and 13.A three-step sequence was used to convert 4 into the β-lactam-pyra

    3-(1'-hydroxyethyl)-2-azetidinones from 3-hydroxybutyrates and N-arylaldimines

    Georg,Gill,Gerhardt

    , p. 3903 - 3906 (2007/10/02)

    Dianion imine addition, cyclisation reaction between ethyl-3-hydroxybutyrate and the aldimines generates β-lactams with the hydroxyethyl side chain of thienamycin and related β-lactam antibiotics in place. The effects of the N-arylaldimine and the reactio

    Process route upstream and downstream products

    Process route

    ethyl 3-hydroxybutyrate
    5405-41-4

    ethyl 3-hydroxybutyrate

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline
    88315-63-3

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

    Conditions
    ConditionsYield
    With lithium cyclohexylisopropylamide;Intetrahydrofuran;the reaction mixture was quenched at 10 deg C;
    77%
    ethyl (S)-3-hydroxybutyrate
    56816-01-4

    ethyl (S)-3-hydroxybutyrate

    <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone
    101977-77-9

    <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

    Conditions
    ConditionsYield
    With n-butyllithium; diisopropylamine;Intetrahydrofuran; hexane;at -78 - 20 ℃; for 22h; Yields of byproduct given;
    25%
    ethyl (S)-3-hydroxybutyrate
    56816-01-4

    ethyl (S)-3-hydroxybutyrate

    N-cinnamylidene-p-anisidine
    80542-40-1

    N-cinnamylidene-p-anisidine

    Conditions
    ConditionsYield
    With lithium diisopropyl amide;Intetrahydrofuran;
    67%
    ethyl 3-hydroxybutyrate
    5405-41-4

    ethyl 3-hydroxybutyrate

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline
    88315-63-3

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

    (3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

    (3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

    Conditions
    ConditionsYield
    With lithium cyclohexylisopropylamide;Intetrahydrofuran;Product distribution; with or without HMPA; the effects of the N-arylaldimine and the reaction conditions on the stereochemistry of the products were examined;
    ethyl 3-hydroxybutyrate
    5405-41-4

    ethyl 3-hydroxybutyrate

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline
    88315-63-3

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

    (3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

    (3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

    Conditions
    ConditionsYield
    With lithium cyclohexylisopropylamide;Intetrahydrofuran;Product distribution; with or without HMPA; the effects of the N-arylaldimine and the reaction conditions on the stereochemistry of the products were examined;
    ethyl 3-hydroxybutyrate
    5405-41-4

    ethyl 3-hydroxybutyrate

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline
    88315-63-3

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

    Conditions
    ConditionsYield
    With lithium cyclohexylisopropylamide;Intetrahydrofuran;the reaction mixture was quenched at 10 deg C;
    77%
    ethyl (S)-3-hydroxybutyrate
    56816-01-4

    ethyl (S)-3-hydroxybutyrate

    <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone
    101977-77-9

    <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

    Conditions
    ConditionsYield
    With n-butyllithium; diisopropylamine;Intetrahydrofuran; hexane;at -78 - 20 ℃; for 22h; Yields of byproduct given;
    25%
    ethyl (S)-3-hydroxybutyrate
    56816-01-4

    ethyl (S)-3-hydroxybutyrate

    N-cinnamylidene-p-anisidine
    80542-40-1

    N-cinnamylidene-p-anisidine

    Conditions
    ConditionsYield
    With lithium diisopropyl amide;Intetrahydrofuran;
    67%
    ethyl 3-hydroxybutyrate
    5405-41-4

    ethyl 3-hydroxybutyrate

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline
    88315-63-3

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

    (3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

    (3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

    Conditions
    ConditionsYield
    With lithium cyclohexylisopropylamide;Intetrahydrofuran;Product distribution; with or without HMPA; the effects of the N-arylaldimine and the reaction conditions on the stereochemistry of the products were examined;
    ethyl 3-hydroxybutyrate
    5405-41-4

    ethyl 3-hydroxybutyrate

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline
    88315-63-3

    (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

    (3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

    (3S,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

    Conditions
    ConditionsYield
    With lithium cyclohexylisopropylamide;Intetrahydrofuran;Product distribution; with or without HMPA; the effects of the N-arylaldimine and the reaction conditions on the stereochemistry of the products were examined;

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