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100009-52-7

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Home > CAS Database list > 100009-52-7

100009-52-7

100009-52-7

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

: 5405-41-4
ethyl 3-hydroxybutyrate

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

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

Conditions	Yield
With lithium cyclohexylisopropylamide;Intetrahydrofuran;the reaction mixture was quenched at 10 deg C;	77%

: 15286-52-9,22835-33-2,80542-40-1,88315-63-3,101535-86-8,123525-44-0
N-(4-Methoxyphenyl)-3-phenylpropenaldimine

: 56816-01-4
ethyl (S)-3-hydroxybutyrate

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3S,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

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

Conditions	Yield
With n-butyllithium; diisopropylamine;Intetrahydrofuran; hexane;at -78 - 20 ℃; for 22h; Yields of byproduct given;	25%

: 56816-01-4
ethyl (S)-3-hydroxybutyrate

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

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

Conditions	Yield
With lithium diisopropyl amide;Intetrahydrofuran;	67%

: 5405-41-4
ethyl 3-hydroxybutyrate

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

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3R,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3S,4R)-3-((S)-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	Yield
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;

: 5405-41-4
ethyl 3-hydroxybutyrate

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

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3R,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3S,4R)-3-((S)-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	Yield
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;

: 5405-41-4
ethyl 3-hydroxybutyrate

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

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

Conditions	Yield
With lithium cyclohexylisopropylamide;Intetrahydrofuran;the reaction mixture was quenched at 10 deg C;	77%

: 15286-52-9,22835-33-2,80542-40-1,88315-63-3,101535-86-8,123525-44-0
N-(4-Methoxyphenyl)-3-phenylpropenaldimine

: 56816-01-4
ethyl (S)-3-hydroxybutyrate

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3S,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

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

Conditions	Yield
With n-butyllithium; diisopropylamine;Intetrahydrofuran; hexane;at -78 - 20 ℃; for 22h; Yields of byproduct given;	25%

: 56816-01-4
ethyl (S)-3-hydroxybutyrate

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

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

Conditions	Yield
With lithium diisopropyl amide;Intetrahydrofuran;	67%

: 5405-41-4
ethyl 3-hydroxybutyrate

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

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3R,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3S,4R)-3-((S)-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	Yield
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;

: 5405-41-4
ethyl 3-hydroxybutyrate

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

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3R,4R)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one

: 100009-52-7,100296-95-5,100296-96-6,101977-76-8,101977-77-9,101977-78-0,101977-79-1,102046-03-7,115184-76-4,115184-77-5,115184-78-6
(3S,4R)-3-((S)-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	Yield
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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