tert-Butyl (R)-(1-oxopropan-2-yl)carbamate

Name: tert-Butyl (R)-(1-oxopropan-2-yl)carbamate
Brand: ChemScene
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CAS No. 82353-56-8
Cat. No. CS-0181955
Purity≥98%
MDL No.MFCD00274183

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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tert-Butyl (R)-(1-oxopropan-2-yl)carbamate|CS-0181955

Structure of 82353-56-8

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General Information

CAS No. 82353-56-8
Cat. No. CS-0181955
Purity ≥98%
MDL No. MFCD00274183
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₅NO₃
Molecular Weight 173.21
Synonym(s) Carbamic acid, [(1R)-1-methyl-2-oxoethyl]-, 1,1-dimethylethyl ester (9CI)
SMILES O=C(OC(C)(C)C)N[C@H](C)C=O

Description

tert-Butyl (R)-(1-oxopropan-2-yl)carbamate is a chiral protecting group reagent featuring a stereodefined (R)-configuration at the prochiral carbon. This bench-stable carbamate delivers selective N-protection in asymmetric synthesis, enabling efficient incorporation into complex peptide architectures and chiral building blocks without racemization.

Application

tert-Butyl (R)-(1-oxopropan-2-yl)carbamate serves as a stereochemically defined chiral auxiliary and protected amino acid precursor, enabling efficient enantioselective synthesis of β-amino carbonyl compounds. Its tert-butyl carbamate group offers excellent bench stability and facilitates straightforward deprotection under mild acidic conditions. The molecule functions reliably in peptide coupling, asymmetric alkylation, and nucleophilic addition reactions, providing high diastereoselectivity in standard synthetic workflows.

Synthesis

Route1
- In-stock
  
  79069-13-9
- ~10%
- In-stock
  
  82353-56-8
References
- Yao, Haoyi; Yamamoto, Kana Chemistry - An Asian Journal, 2012 , vol. 7, # 7 p. 1542 - 1545
Route2
- In-stock
  
  91103-47-8
- ~94%
- In-stock
  
  82353-56-8
References
- Chakravarty, Prasun K.; Greenlee, William J.; Parsons, William H.; Patchett, Arthur A.; Combs, Patricia; et al. Journal of Medicinal Chemistry, 1989 , vol. 32, # 8 p. 1886 - 1890
Route3
- In-stock
  
  146553-06-2
- ~73%
- In-stock
  
  82353-56-8
References
- Boger, Dale L.; Menezes, Royce F. Journal of Organic Chemistry, 1992 , vol. 57, # 16 p. 4331 - 4333 Title/Abstract Full Text View citing articles Show Details Boger, Dale L.; Colletti, Steven L.; Honda, Takeshi; Menezes, Royce F. Journal of the American Chemical Society, 1994 , vol. 116, # 13 p. 5607 - 5618

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 55.4
LogP 1.0985
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Amine

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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tert-Butyl (R)-(1-oxopropan-2-yl)carbamate

CAS No. 82353-56-8

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