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Merck
CN

410438

Methyl (S)-(−)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate

98%

Synonym(s):

Methyl (S)-(−)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate

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About This Item

Empirical Formula (Hill Notation):
C12H21NO5
CAS Number:
108149-60-6
Molecular Weight:
259.30
NACRES:
NA.22
PubChem Substance ID:
24865525
UNSPSC Code:
12352005
MDL number:
MFCD00192279

Key Documents

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Product Name

Methyl (S)-(−)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate, 98%

InChI

1S/C12H21NO5/c1-11(2,3)18-10(15)13-8(9(14)16-6)7-17-12(13,4)5/h8H,7H2,1-6H3/t8-/m0/s1

SMILES string

COC(=O)[C@@H]1COC(C)(C)N1C(=O)OC(C)(C)C

InChI key

ZNBUXTFASGDVCL-QMMMGPOBSA-N

assay

98%

form

liquid

optical activity

[α]20/D −55°, c = 1.3 in chloroform

optical purity

ee: 99% (HPLC)

refractive index

n20/D 1.443 (lit.)

bp

101-102 °C/2 mmHg (lit.)

density

1.082 g/mL at 25 °C (lit.)

functional group

ester
ether

Application

Precursor to a configurationally stable serinal derivative (Garner′s aldehyde) that has been used to make azasugars, sphingolipids, and the amino sugar found in calicheamicin, a potent antitumor agent.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

199.4 °F - closed cup

flash_point_c

93 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
04531CJ
08714AJ
13228LH
06025HH
04315BE

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Koskinen, A.M.P. et al.
Synlett, 665-665 (1990)
Kahne, D. et al.
Tetrahedron Letters, 31, 21-21 (1990)
Garner, P. Park, J.M.
J. Org. Synth., 70, 18-18 (1992)
Garner, P. Park, J.M.
The Journal of Organic Chemistry, 52, 2361-2361 (1987)
Dondoni, A. et al.
Journal of the Chemical Society. Chemical Communications, 1576-1576 (1991)

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