(S)-tert-butyl 1-hydroxy-3-phenylpropan-2-ylcarbamate

Name: (S)-tert-butyl 1-hydroxy-3-phenylpropan-2-ylcarbamate
Brand: ChemScene
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CAS No. 66605-57-0
Cat. No. CS-M0537
Purity≥98%
MDL No.MFCD00076976

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(S)-tert-butyl 1-hydroxy-3-phenylpropan-2-ylcarbamate|CS-M0537

Structure of 66605-57-0

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General Information

CAS No. 66605-57-0
Cat. No. CS-M0537
Purity ≥98%
MDL No. MFCD00076976
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₁NO₃
Molecular Weight 251.32
Synonym(s) None
SMILES O=C(OC(C)(C)C)N[C@H](CO)CC1=CC=CC=C1

Description

(S)-tert-Butyl 1-hydroxy-3-phenylpropan-2-ylcarbamate is a chiral, bench-stable building block featuring a hydroxylated prochiral center flanked by a phenyl group and a carbamate-protected amine. This configuration enables stereoselective transformations in asymmetric synthesis, particularly in the construction of complex amino alcohols and β-aryl-α-amino acid derivatives.

Application

(S)-tert-Butyl 1-hydroxy-3-phenylpropan-2-ylcarbamate serves as a chiral building block for the synthesis of bioactive molecules, enabling stereoselective construction of α-hydroxy-α-amino acid derivatives. The protected hydroxyamine functionality facilitates controlled functionalization and orthogonal transformations, while the tert-butyl carbamate group provides stability and ease of purification. Its bench-stable nature and compatibility with standard coupling and deprotection protocols make it well-suited for medicinal chemistry campaigns requiring precise stereocontrol.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 3182-95-4
- ~99%
- In-stock
  
  66605-57-0
References
- Kerherve, Jennifer; Botuha, Candice; Dubois, Joelle Organic and Biomolecular Chemistry, 2009 , vol. 7, # 10 p. 2214 - 2222
Route2
- 4522-04-7
- ~89%
- In-stock
  
  66605-57-0
References
- Soai; Oyamada; Takase Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 8 p. 2327 - 2328
Route3
- 1025839-59-1
- ~84%
- In-stock
  
  66605-57-0
References
- Falorni, Massimo; Giacomelli, Giampaolo; Porcheddu, Andrea; Taddei, Maurizio Journal of Organic Chemistry, 1999 , vol. 64, # 24 p. 8962 - 8964

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 58.56
LogP 2.1147
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

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(S)-tert-butyl 1-hydroxy-3-phenylpropan-2-ylcarbamate

CAS No. 66605-57-0

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