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917125

Sigma-Aldrich

tert-Butyl 4-(4-(hydroxymethyl)phenyl)piperidine-1-carboxylate

≥95%

Synonym(s):

Semi-flexible linker for PROTAC® development

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About This Item

Empirical Formula (Hill Notation):
C17H25NO3
CAS Number:
864359-18-2
Molecular Weight:
291.39
MDL number:
MFCD18452163
UNSPSC Code:
12352116

Quality Level

100

assay

≥95%

form

chunks

reaction suitability

reagent type: linker

functional group

Boc
hydroxyl

storage temp.

2-8°C

SMILES string

O=C(N(CC1)CCC1C(C=C2)=CC=C2CO)OC(C)(C)C

InChI

1S/C17H25NO3/c1-17(2,3)21-16(20)18-10-8-15(9-11-18)14-6-4-13(12-19)5-7-14/h4-7,15,19H,8-12H2,1-3H3

InChI key

YPAVHCJZNOTJLF-UHFFFAOYSA-N

Application

tert-Butyl 4-(4-(hydroxymethyl)phenyl)piperidine-1-carboxylate is a 4-aryl piperidine useful as a semi-flexible linker in PROTAC development for targeted protein degradation. Incorporation of rigidity into the linker region of bifunctional protein degraders may impact the 3D orientation of the degrader and thus ternary complex formation as well as optimization of drug-like properties.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Crosslinkers for Bioconjugation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

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pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Peter S Campbell et al.
Chemical communications (Cambridge, England), 54(1), 46-49 (2017-12-01)
The expedient synthesis of compounds enriched in sp3 character is key goal in modern drug discovery. Herein, we report how a single pot Suzuki-Miyaura-hydrogenation can be used to furnish lead and fragment-like products in good to excellent yields. The approach

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