(R)-Methyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate

Name: (R)-Methyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate
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CAS No. 95715-85-8
Cat. No. CS-W019796
Purity≥95%
MDL No.MFCD00270516

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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(R)-Methyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate|CS-W019796

Structure of 95715-85-8

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General Information

CAS No. 95715-85-8
Cat. No. CS-W019796
Purity ≥95%
MDL No. MFCD00270516
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₇NO₅
Molecular Weight 219.23
Synonym(s) tert-Butyl [(R)-1-(methoxycarbonyl)-2-hydroxyethyl]carbamate
SMILES OC[C@@H](NC(OC(C)(C)C)=O)C(OC)=O

Description

(R)-Methyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate is a stereochemically defined chiral building block featuring a protected amino group and a hydroxyl-bearing carbon. This configuration enables selective incorporation into peptide backbones and complex natural product syntheses, where precise stereocontrol is essential. The tert-butyl carbamate moiety ensures stability during multi-step transformations and can be removed under mild acidic conditions.

Application

(R)-Methyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate serves as a key chiral building block for synthesizing β-amino alcohols and peptidomimetics. The protected amine and hydroxyl groups enable orthogonal functionalization, while the methyl ester supports subsequent transformations. Bench-stable and readily purified by chromatography, it functions effectively in standard coupling and reduction protocols for complex molecule assembly.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 2104-89-4
- ~92%
- In-stock
  
  95715-85-8
References
- Tetrahedron Letters, , vol. 36, # 39 p. 7031 - 7034
Route2
- In-stock
  
  3262-72-4
- 74-88-4
- ~98%
- In-stock
  
  95715-85-8
References
- Journal of the American Chemical Society, , vol. 116, # 18 p. 8402 - 8403
Route3
- In-stock
  
  24424-99-5
- In-stock
  
  5874-57-7
- ~99%
- In-stock
  
  95715-85-8
References
- Organic Letters, , vol. 15, # 10 p. 2474 - 2477

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 84.86
LogP 0.045
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Serine and derivatives

Life Science Amino Acids and their Derivatives C-protected amino acid

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

Biochemistry Biochemicals and Reagents Amino Acids C-ProtectedAmino Acids

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

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(R)-Methyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate

CAS No. 95715-85-8

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