ChemicalBook > CAS DataBase List > (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

Product Name
(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
CAS No.
76855-69-1
Chemical Name
(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
Synonyms
4-AA;4-ACETOXYAZETIDIN-2-ONE;(3R,4R)-4-ACETOXY-3-[(R)-(T-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE;(3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]AZETIDIN-2-ONE;4-AOSA;(3R<;Azetidon;4AA(AOSA);AOSA (4-AA);4-AA or 4-AOSA
CBNumber
CB0458274
Molecular Formula
C13H25NO4Si
Formula Weight
287.43
MOL File
76855-69-1.mol
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(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Property

Melting point:
107-109 °C(lit.)
alpha 
51 º (c=1, chloroform)
Boiling point:
358.3±27.0 °C(Predicted)
Density 
1.03±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
almost transparency in Methanol
form 
powder to crystal
pka
12.86±0.60(Predicted)
color 
White to Almost white
optical activity
[α]20/D +51°, c = 1 in chloroform
InChI
InChI=1S/C13H25NO4Si/c1-8(18-19(6,7)13(3,4)5)10-11(16)14-12(10)17-9(2)15/h8,10,12H,1-7H3,(H,14,16)/t8-,10+,12-/m1/s1
InChIKey
GWHDKFODLYVMQG-UBHAPETDSA-N
SMILES
N1[C@H](OC(C)=O)[C@@H]([C@H](O[Si](C(C)(C)C)(C)C)C)C1=O
CAS DataBase Reference
76855-69-1(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi,N
Risk Statements 
36-43-51/53
Safety Statements 
24-26-37-61
RIDADR 
UN 3077 9/PG 3
WGK Germany 
2
HazardClass 
9
PackingGroup 
III
HS Code 
29337900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
375845
Product name
[3R(1′R,4R)]-(+)-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
Purity
98%
Packaging
1g
Price
$112.7
Updated
2025/07/31
TCI Chemical
Product number
A1124
Product name
(3R,4R)-4-Acetoxy-3-[(R)-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
Purity
>98.0%(N)
Packaging
5g
Price
$234
Updated
2025/07/31
TCI Chemical
Product number
A1124
Product name
(3R,4R)-4-Acetoxy-3-[(R)-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
Purity
>98.0%(N)
Packaging
25g
Price
$846
Updated
2025/07/31
TRC
Product number
A164500
Product name
(3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
Packaging
1g
Price
$65
Updated
2021/12/16
AK Scientific
Product number
J99423
Product name
(3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
Packaging
25g
Price
$49
Updated
2021/12/16
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(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powde

Uses

(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one is an acetoxyazetidinone derivative used as an intermediate in the preparation of carbapenem antibiotics.

Purification Methods

Purify it by chromatography on silica gel (3 x 14cm) for 50g of ester using 20% EtOAc in n-hexane. The eluate is evaporated, and the residue is recrystallised from hexane (white fluffy crystals). [Leanza et al. Tetrahedron 39 2505 1983.]

(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Preparation Products And Raw materials

Raw materials

Ethyl acetoacetate Sodium hypochlorite Acetonitrile (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Ethanol Acetic anhydride Potassium hydroxide (R)-(+)-1,1'-Bi-2-naphthol tert-Butyldimethylsilyl chloride Triethyl orthoformate 2-Mercaptothiazoline Ruthenium(III) chloride Oxygen Triethylamine Palladium (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE Benzamide Hydrochloric acid Hydrogen Dichloromethane 1,5-Cyclooctadiene Methanol tert-Butylamine

Preparation Products

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(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one Suppliers

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View Lastest Price from (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 76855-69-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98.0%
Supply Ability
10000KGS
Release date
2024-11-14
Xinxiang Hongqi District Houyuan Trading Co.,Ltd
Product
(3S,4R) -4-acetoxy-3 -[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 76855-69-1
Price
US $30.00-28.00/Kg
Min. Order
1Kg
Purity
99.0% up
Supply Ability
50 tons per month
Release date
2022-10-07
Xinxiang Hongqi District Houyuan Trading Co.,Ltd
Product
(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
Price
US $30.00-28.00/Kg
Min. Order
1Kg
Purity
99.0% up
Supply Ability
50 tons per month
Release date
2022-09-21

76855-69-1, (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-oneRelated Search:

Benzyloxyacetyl chloride N-Methyl-2-pyrrolidone Ethyl formate Ethyl propionate Ethyl acrylate Ethylparaben 2-Butanone oxime Sodium triacetoxyborohydride Ethanol Diethoxydimethylsilane Ethylbenzene Dimethyldimethoxysilane Laurocapram 2-Azetidinone Diltiazem hydrochloride 4-Acetoxystyrene Ethyl acetate T-BUTYLDIMETHYLSILANE

  • 4-AA
  • (3s,4r)-4-acetoxy-3-[(r)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
  • (3R,4R)-(+)-4-ACETOXY-3-[(R)-(T-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE
  • (3R,4R)-4-ACETOXY-3-[(R)-(T-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE
  • (3R,4R)-4-ACETOXY-3-[(R)-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE
  • (3R,4R)-4-(ACETYLOXY)-3-[(1R)-1-[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]ETHYL]-2-AZETIDINONE
  • [3R(1'R,4R)]-(+)-4-ACETOXY-3-[1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE
  • (2R,3R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-4-OXOAZETIDIN-2-YLACETATE
  • 4-AOSA
  • (3R,4R)-4-acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
  • 2-Azetidinone, 4-(acetyloxy)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-, (3R,4R)-
  • acetoxyazetidinone
  • (3S,4R)-4-acetoxy-3-[-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
  • (R R(R))-4-ACETOXY-3-(1-TBDMS-OXY)-
  • (3R(1'R,4R))-(+)-4-ACETOXY-3-(1-(T-BUTYL DI -METHYLSILYLOXY)ETH)-2-AZETIDINONE,98
  • 4-ACETOXYAZETIDIN-2-ONE
  • [3R(1′R,4R)]-(+)-4-Acetoxy-3-[1-(tert-butyldimeth
  • (3R,4R)-4-ACETOXY-3-[(3R)-TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE
  • 4-ACETOXYAZETIDINE-2-ONE( 4-AA, ABA, AOSA)
  • (3S)-4-(4'-Fluorophenyl)-3-eth
  • （3S,4R）-4-Acetoxy-3-[(R)-1-(tert-butyl
  • 4-AA (INTERMEDIATE OF CARTAPENEM)
  • 4-ACETOXYAZETIDIN-2-ONE (4-AA , 4-ABA OR 4-AOSA)
  • 4-ACETOXYAZETIDIN-2-ONE 4-AA(AOSA)(PENEM INTERMEDIATE )
  • 4-acetoxyazetidin-2-one(4AA)
  • ACETOXYSILYLOXYAZETIDINONE
  • (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]AZETIDIN-2-ONE
  • 4-Acetoxysilyloxyazetidinone
  • [3R(1''R)4R]-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)-ethyl]-2-azetidinon
  • 4AA(AOSA)
  • (2R,3R)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-4-oxoazetidin-2-yl acetate
  • (2R,3R)-3-((R)-1-(tert-butyldimethylsiloxy)ethyl)-4-oxoazetidin-2-yl acetate
  • 4-AA or 4-AOSA
  • 4-acetoxy-3-[1-(butyldimethylsilyloxy)ethyl]-2-azetidinone
  • [3R(1R),4R]-4-Acetoxy-3-[1-(tert-butyldimethylsiloxy)ethyl]-2-azetidinone
  • Carbapenem intermediate: Acetoxyazetidinone
  • (3<i>R</i>,4<i>R</i>)-4-Acetoxy-3-[(<i>R</i>)-(<i>tert</i>-butyldimethylsilyloxy)ethyl]-2-azetidinone
  • ACETOXYSILYLOXYAZETIDINONE(AOSA)
  • 4- acetoxy azetidone
  • (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one AOSA (4-AA)
  • 3R, 4R)-4-acetoxy-3-[(1R)-1-t-butyldimethylsilyloxyethyl]azetidin-2-one
  • intermediates of Meropenem
  • (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidinone
  • AOSA (4-AA)
  • (3R,4R)-4-Acetoxy-3-[(R)-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone ,98%
  • (3S,4R)-4-Acetoxy-3-
  • (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
  • 3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldiMethylsilyloxy)ethyl]-2-a
  • 3-(1-(ButyldiMethylsilyloxy)ethyl)-4-oxoazetidin-2-yl acetate
  • (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldiMethylsilyoxy)ethyl]azetidin-2-one
  • (1'R,3R,4R)-4-Acetoxy-3-(1'-tert-butyldiMethylsilyloxyethyl)-2-azetidinone
  • (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldiMethylsiloxy)ethyl]azetidin-2-one
  • (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldiMethylsilyloxy)ethyl]azetidinone
  • [3R-[3α(R*),4β]]-4-(Acetyloxy)-3-[1-[[(1,1-diMethylethyl)diMethylsilyl]oxy]ethyl]-2-azetidinone
  • (3R,4R)-(+)-4-Acetoxy-3-[1-(R)-(tert-butyldiMethylsilyloxy)ethyl]-2-azetidinone, 98%
  • (2R,3S)-3-[(1R)-1-[(tert-butyldiMethylsilyl)oxy]ethyl]-4-oxoazetidin-2-yl acetate
  • 4-AA ((2R,3R)-3-((R)-1-(tert-Butyldimethylsilyloxy)ethyl)-4-oxoazetidin-2-yl acetate)
  • (3S 4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethy