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Cas Database

101977-77-9

101977-77-9

Identification

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

  • CAS Number: 101977-77-9

  • EINECS:

  • Molecular Weight:323.392

  • Molecular Formula: C20H21NO3

  • HS Code:

  • Mol File:101977-77-9.mol

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

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Relevant articles and documentsAll total 5 Articles be found

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

Stereospecific Synthesis of a Chiral Intermediate for the Preparation of Thienamycin, Penems, and Carbapenems: Use of the Nitro Group as a Hydroxy Protecting Group

Cainelli, Gianfranco,Panunzio, Mauro,Basile, Tiziana,Bongini, Alessandro,Giacomini, Daria,Martelli, Giorgio

, p. 2637 - 2642 (2007/10/02)

A total stereo- and enantio-controlled synthesis of (3S,4R)-4-acetoxy-3-azetidin-2-one (1) from ethyl (S)-3-hydroxybutyrate is reported.A simple method of inversion and concomitant protection of the hydroxy function in the side chain i

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.

AN ENANTIOSELECTIVE APPROACH TO CARBAPENEM ANTIBIOTICS: FORMAL SYNTHESIS OF (+)-THIENAMYCIN

Hart, David J.,Ha, Deok-Chan

, p. 5493 - 5496 (2007/10/02)

An enantioselective synthesis of intermediates in synthesis of thienamycin (15) and epithienamycin-C (16) is described.

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
Conditions Yield
With lithium cyclohexylisopropylamide; In tetrahydrofuran; 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
Conditions Yield
With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 22h; Yields of byproduct given;
25%
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
Conditions Yield
With n-butyllithium; diisopropylamine; In tetrahydrofuran; 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
Conditions Yield
With lithium diisopropyl amide; In tetrahydrofuran;
67%
ethyl (S)-3-hydroxybutyrate
56816-01-4

ethyl (S)-3-hydroxybutyrate

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

N-cinnamylidene-p-anisidine

(3S,4R)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one
101977-76-8

(3S,4R)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one

(3R,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one
102046-03-7

(3R,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one

<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
Conditions Yield
With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, - 70 deg C; 2.) room temperature, 20 h;
With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, - 70 deg C; 2.) room temperature 20 h;
With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, - 70 deg C; 2.) room temperature, 20 h;
With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction. Yields of byproduct given; 1.) hexane, r.t., 15 min; 2.) hexane, THF, 1 h; 3.) THF, r.t.;
With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction. Yields of byproduct given; 1.) hexane, r.t., 15 min; 2.) hexane, THF, 1 h; 3.) toluene, r.t.;
(S)-3-hydroxybutyric acid methyl ester
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

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

N-cinnamylidene-p-anisidine

(3S,4R)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one
101977-76-8

(3S,4R)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one

(3R,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one
102046-03-7

(3R,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one

<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
Conditions Yield
With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction. Yields of byproduct given; 1.) hexane, r.t., 15 min; 2.) hexane, THF, 1 h; 3.) THF, r.t.;
N-cinnamylidene-p-anisidine
80542-40-1

N-cinnamylidene-p-anisidine

tert-butyl (S)-3-hydroxybutyrate
82578-45-8

tert-butyl (S)-3-hydroxybutyrate

(3S,4R)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one
101977-76-8

(3S,4R)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one

(3R,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one
102046-03-7

(3R,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one

<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
Conditions Yield
With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction. Yields of byproduct given; 1.) hexane, r.t., 15 min; 2.) hexane, THF, 1 h; 3.) THF, r.t.;
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
Conditions Yield
With lithium cyclohexylisopropylamide; In tetrahydrofuran; 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
Conditions Yield
With lithium cyclohexylisopropylamide; In tetrahydrofuran; 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 (S)-3-hydroxybutyrate
56816-01-4

ethyl (S)-3-hydroxybutyrate

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

N-cinnamylidene-p-anisidine

<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

(3R,4S(E))-3-(1(S)-(((1,1-dimethylethyl)dimethylsilyl)oxy)ethyl)-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone
102129-92-0

(3R,4S(E))-3-(1(S)-(((1,1-dimethylethyl)dimethylsilyl)oxy)ethyl)-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

(1'S,3S,4R)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone
101977-84-8

(1'S,3S,4R)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone

Conditions
Conditions Yield
Yield given. Multistep reaction. Yields of byproduct given;

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