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Merck
CN

375845

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

98%

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About This Item

Empirical Formula (Hill Notation):
C13H25NO4Si
CAS Number:
76855-69-1
Molecular Weight:
287.43
NACRES:
NA.22
PubChem Substance ID:
24863408
UNSPSC Code:
12352005
EC Number:
408-050-9
MDL number:
MFCD00077636
Assay:
98%

Key Documents

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Product Name

[3R(1′R,4R)]-(+)-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone, 98%

InChI key

GWHDKFODLYVMQG-UBHAPETDSA-N

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

SMILES string

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

assay

98%

optical activity

[α]20/D +51°, c = 1 in chloroform

mp

107-109 °C (lit.)

functional group

ester

storage temp.

2-8°C

Quality Level

100

Related Categories

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT1974
MKBP5117V
00620TD
11815BD
04903BD

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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

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