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Cas Database

201856-48-6

201856-48-6

Identification

  • Product Name:(3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone

  • CAS Number: 201856-48-6

  • EINECS:

  • Molecular Weight:235.283

  • Molecular Formula: C13H17NO3

  • HS Code:

  • Mol File:201856-48-6.mol

Synonyms:(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone;(3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone;2-Azetidinone,3-(1-ethoxyethoxy)-4-phenyl;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 7 Articles be found

A [...] he [...] synthesis process

-

Paragraph 0013, (2019/04/06)

A [...] he [...] synthesis process, in order to (3 R, 4 S) - 3 - hydroxy - 4 - phenyl - 2 - azetidinone as the starting material, adopts the one-pot synthesis, its first with vinyl ether condensation, with the BOC - anhydride is condensed directly [...] h

Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment

-

, (2008/06/13)

The present invention is directed to novel taxanes useful as chemotherapeutic agents or their precursors. Processes for preparing the novel taxanes include coupling reactions, in the presence of a base, of baccatin of formula (III) or (IV) STR1 with β-lac

Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment

-

, (2008/06/13)

The present invention is directed to novel taxanes useful as chemotherapeutic agents or their precursors. Processes for preparing the novel taxanes include coupling reactions, in the presence of a base, of baccatin of formula (III) or (IV) STR1 with β-lac

A highly efficient route to taxotere by the β-lactam synthon method

Ojima, Iwao,Sun, Chung Ming,Zucco, Martine,Park, Young Boon,Duclos, Olivier,Kuduk, Scott

, p. 4149 - 4152 (2007/10/02)

Taxotere, a highly promising anticancer drug, is synthesized through an efficient coupling of 7,10-diTroc-10-deacetylbaccatin III with enantiomerically pure (3R,4S)-1-tBOC-3-EEO- 4-phenylazetidin-2-one which is obtained via chiral ester enolate - imine cyclocondensation.

New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Ojima, Iwao,Habus, Ivan,Zhao, Mangzhu,Zucco, Martine,Park, Young Hoon,Sun, Chung Ming,Brigaud, Thierry

, p. 6985 - 7012 (2007/10/02)

Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.

Process route upstream and downstream products

Process route

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
132127-34-5

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

ethyl vinyl ether
109-92-2,25104-37-4

ethyl vinyl ether

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
With hydrogen cation;
100%
In tetrahydrofuran; at 0 ℃; for 2h;
100%
With toluene-4-sulfonic acid; In tetrahydrofuran; for 0.5h;
95%
With methanesulfonic acid; In tetrahydrofuran; at 0 ℃;
(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one
132127-31-2

(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 100 percent / NBu4F / tetrahydrofuran
2: 100 percent / H(1+)
With tetrabutyl ammonium fluoride; hydrogen cation; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: 98 percent / n-Bu4NF / tetrahydrofuran / 1 h / Ambient temperature
2: 95 percent / p-TSA / tetrahydrofuran / 0.5 h
With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran;
methanesulfonic acid
75-75-2,98527-29-8

methanesulfonic acid

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
132127-34-5

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

ethyl vinyl ether
109-92-2,25104-37-4

ethyl vinyl ether

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
In tetrahydrofuran; hexane; acetone;
4.87 g (99%)
N-benzylidene-1,1,1-trimethylsilanamine
17599-61-0

N-benzylidene-1,1,1-trimethylsilanamine

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
2: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
3: 100 percent / tetrahydrofuran / 2 h / 0 °C
With n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran;
Multi-step reaction with 3 steps
1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
2: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
3: 100 percent / tetrahydrofuran / 2 h / 0 °C
With n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran;
benzaldehyde
100-52-7

benzaldehyde

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 1. hexamethyldisilazane, n-BuLi / 1. THF, hexane, reflux, 3 h; 2. reflux, 2 h
2: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
3: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
4: 100 percent / tetrahydrofuran / 2 h / 0 °C
With n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran;
Multi-step reaction with 4 steps
1: 1. hexamethyldisilazane, n-BuLi / 1. THF, hexane, reflux, 3 h; 2. reflux, 2 h
2: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.
3: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
4: 100 percent / tetrahydrofuran / 2 h / 0 °C
With n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran;
3-Triisopropylsilyloxy-4-phenylazetidin-2-one
132127-31-2,132201-31-1

3-Triisopropylsilyloxy-4-phenylazetidin-2-one

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature
2: 100 percent / tetrahydrofuran / 2 h / 0 °C
With tetrabutyl ammonium fluoride; In tetrahydrofuran;
(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
132127-34-5

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

ethyl vinyl ether
109-92-2,25104-37-4

ethyl vinyl ether

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
With hydrogen cation;
100%
In tetrahydrofuran; at 0 ℃; for 2h;
100%
With toluene-4-sulfonic acid; In tetrahydrofuran; for 0.5h;
95%
With methanesulfonic acid; In tetrahydrofuran; at 0 ℃;
(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one
132127-31-2

(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 100 percent / NBu4F / tetrahydrofuran
2: 100 percent / H(1+)
With tetrabutyl ammonium fluoride; hydrogen cation; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: 98 percent / n-Bu4NF / tetrahydrofuran / 1 h / Ambient temperature
2: 95 percent / p-TSA / tetrahydrofuran / 0.5 h
With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran;
methanesulfonic acid
75-75-2,98527-29-8

methanesulfonic acid

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
132127-34-5

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

ethyl vinyl ether
109-92-2,25104-37-4

ethyl vinyl ether

(3R,4S)-3-<((R<sup>*</sup>)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone
201856-48-6

(3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

Conditions
Conditions Yield
In tetrahydrofuran; hexane; acetone;
4.87 g (99%)

Global suppliers and manufacturers

Global( 4) Suppliers
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  • Emails
  • Main Products
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  • Antimex Chemical Limied
  • Business Type:Lab/Research institutions
  • Contact Tel:0086-21-50563169
  • Emails:anthony@antimex.com
  • Main Products:163
  • Country:China (Mainland)
  • Career Henan Chemical Co
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-371-86658258
  • Emails:purchase@coreychem.com
  • Main Products:1
  • Country:China (Mainland)
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