Skip to Content
Merck
All Photos(2)

Documents

375845

Sigma-Aldrich

[3R(1′R,4R)]-(+)-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

98%

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C13H25NO4Si
CAS Number:
76855-69-1
Molecular Weight:
287.43
EC Number:
408-050-9
MDL number:
MFCD00077636
UNSPSC Code:
12352005
PubChem Substance ID:
24863408
NACRES:
NA.22

Quality Level

100

Assay

98%

optical activity

[α]20/D +51°, c = 1 in chloroform

mp

107-109 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@@H](O[Si](C)(C)C(C)(C)C)C1[C@H](NC1=O)OC(C)=O

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

InChI key

GWHDKFODLYVMQG-UBHAPETDSA-N

Related Categories

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H317,H319,H411

Hazard Classifications

Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Barbara Grzeszczyk et al.
The Journal of antibiotics, 66(3), 161-163 (2013-03-28)
A novel, practical and stereoselective synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, a key intermediate in the preparation of β-lactam antibiotics is reported. The crucial step of the synthesis is based on the Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade between silyl protected (R)-3-butyn-2-ol and the nitrone

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service