tert-Butyl (S)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate,98% stabilized with TBC

Name: tert-Butyl (S)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate,98% stabilized with TBC
Brand: ChemScene
Availability: InStock
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CAS No. 133625-87-3
Cat. No. CS-0134579
Molecule weightNone
Purity96% (stabilized with TBC)
MDL No.MFCD09033561

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tert-Butyl (S)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate,98% stabilized with TBC|CS-0134579

Structure of 133625-87-3

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General Information

CAS No. 133625-87-3
Cat. No. CS-0134579
Purity 96% (stabilized with TBC)
MDL No. MFCD09033561
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₁NO₃
Molecular Weight None
Synonym(s) Tert-butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
SMILES O=C(N1C(C)(C)OC[C@@H]1C=C)OC(C)(C)C

Description

This bench-stable, moisture-tolerant oxazolidine derivative features a sterically hindered tert-butyl ester and a vinyl group enabling facile cross-coupling. The (S)-configuration provides stereochemical control in asymmetric synthesis, while the TBC stabilizer prevents polymerization during storage and handling.

Application

tert-Butyl (S)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate serves as a versatile chiral building block for asymmetric synthesis, enabling efficient access to enantioselective transformations via its vinylogous amide reactivity. The stabilized form ensures excellent bench shelf life and compatibility with standard coupling protocols. Its robust functional group tolerance facilitates integration into complex molecule assembly, particularly in the construction of heterocyclic scaffolds and peptidomimetics.

Synthesis

Route1
- 1779-49-3
- In-stock
  
  95715-87-0
- ~80%
- In-stock
  
  133625-87-3
References
- Keyes, Robert F.; Carter, Justin J.; Zhang, Xiaolin; Ma, Zhenkun Organic Letters, 2005 , vol. 7, # 5 p. 847 - 849
Route2
- In-stock
  
  2065-66-9
- In-stock
  
  95715-87-0
- ~63%
- In-stock
  
  133625-87-3
References
- Takahata, Hiroki; Banba, Yasunori; Ouchi, Hidekazu; Nemoto, Hideo; Kato, Atsushi; Adachi, Isao Journal of Organic Chemistry, 2003 , vol. 68, # 9 p. 3603 - 3607
Route3
- In-stock
  
  95715-87-0
- 18107-18-1
- ~%
- 115378-31-9
- In-stock
  
  133625-87-3
References
- Angewandte Chemie - International Edition, , vol. 40, # 15 p. 2887 - 2890

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 38.77
LogP 2.5444
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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tert-Butyl (S)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate,98% stabilized with TBC

CAS No. 133625-87-3

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