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375845

Sigma-Aldrich

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

98%

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1 G
¥9,190

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1 G
¥9,190

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

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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

375845-1G:
375845-VAR:
375845-250MG:
375845-BULK:

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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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