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Sigma-Aldrich

N-(tert-Butoxycarbonyl)-p-toluenesulfonamide

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About This Item

Linear Formula:
CH3C6H4SO2NHCO2C(CH3)3
CAS Number:
18303-04-3
Molecular Weight:
271.33
MDL number:
MFCD00134267
UNSPSC Code:
12352100
PubChem Substance ID:
24862365
NACRES:
NA.22

mp

121-123 °C (lit.)

solubility

chloroform: soluble 25 mg/mL, clear, colorless

SMILES string

Cc1ccc(cc1)S(=O)(=O)NC(=O)OC(C)(C)C

InChI

1S/C12H17NO4S/c1-9-5-7-10(8-6-9)18(15,16)13-11(14)17-12(2,3)4/h5-8H,1-4H3,(H,13,14)

InChI key

DUTLOVSBVBGNDM-UHFFFAOYSA-N

General description

N-(tert-Butoxycarbonyl)-p-toluenesulfonamide is a N-substituted sulphonamide and its reaction with N-trityl L-serine esters under Mitsunobu reaction conditions is reported. It can be directly coupled with primary, secondary and allylic alcohols under Mitsunobu conditions to afford various sulfonyl-protected amines.

Application

N-(tert-Butoxycarbonyl)-p-toluenesulfonamide may be used in the preparation of enyne amide, precursor for Pauson-Khand reaction.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Tetrahedron Letters, 30, 5709-5709 (1989)
Toshio Honda et al.
The Journal of organic chemistry, 72(17), 6541-6547 (2007-07-31)
Diastereoselective formal synthesis of a monoterpene alkaloid, (-)-incarvilline, the key intermediate for the synthesis of (-)-incarvillateine, was achieved by using an intramolecular Pauson-Khand reaction of (S)-N-[(E)-2-butenyl]-N-(3-butynyl-2-methoxymethoxy)-p-toluenesulfonamide as a key step.
Use of the Mitsunobu reaction in the synthesis of orthogonally protected a, ?-diaminopropionic acids.
Kelleher F.
Tetrahedron Letters, 48(28), 4879-4882 (2007)

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