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AB46723

61478-26-0 | N-Boc-trans-4-hydroxy-L-prolinol

Packsize Purity Availability Price Discounted Price    Quantity
250mg 97% in stock $6.00 $4.00 -   +
1g 97% in stock $7.00 $5.00 -   +
5g 98% in stock $18.00 $12.00 -   +
10g 98% in stock $20.00 $14.00 -   +
25g 98% in stock $46.00 $32.00 -   +

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*All prices are in USD.

Description
Catalog Number: AB46723
Chemical Name: N-Boc-trans-4-hydroxy-L-prolinol
CAS Number: 61478-26-0
Molecular Formula: C10H19NO4
Molecular Weight: 217.2622
MDL Number: MFCD00040581
SMILES: OC[C@@H]1C[C@H](CN1C(=O)OC(C)(C)C)O

 

Computed Properties
Complexity: 236  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 2  
Heavy Atom Count: 15  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 2  
Rotatable Bond Count: 3  

 

 

Upstream Synthesis Route
  • The upstream synthesis route of N-Boc-trans-4-hydroxy-L-prolinol typically involves the following steps:
    
    1. **Start with L-Prolinol:** We begin with L-prolinol as the chiral starting material. This molecule already contains the secondary alcohol and the pyrrolidine ring central to our target molecule.
    
    2. **Boc-Protection of the Amine:** The amine group of L-prolinol is protected using di-tert-butyl dicarbonate (Boc2O) in the presence of a base, commonly triethylamine (Et3N), to yield N-Boc-L-prolinol. This step prevents unwanted reactions at the amine site during subsequent modification of the hydroxyl group.
    
    3. **Stereochemical Adjustment:** If the starting L-prolinol is not in the trans configuration relative to the hydroxyl group, an epimerization step would be required. This can involve a Mitsunobu reaction that allows inversion of stereochemistry at the secondary alcohol, promoting the formation of the trans-isomer. Alternatively, the starting L-prolinol can be selected to be of the trans configuration, negating the need for this step.
    
    4. **Introduction of the Hydroxyl Group:** In cases where the starting L-prolinol does not have the hydroxy group in the desired position, chemical modification would be necessary. For instance, oxidation of a corresponding alkene precursor followed by reduction could introduce the hydroxyl group at the 4-position with the correct stereochemistry.
    
    5. **Purification:** The reaction mixture would likely be purified by column chromatography, exploiting differences in polarity to separate the desired N-Boc-trans-4-hydroxy-L-prolinol from by-products and unreacted starting materials.
    
    6. **Verification:** The product's structure and purity could be verified using methods such as NMR (nuclear magnetic resonance), LC-MS (liquid chromatography-mass spectrometry), and optical rotation measurements to ensure the correct stereochemistry.
    
    This synthesis route assumes that readily available chemical reagents and standard laboratory equipment are used. It also assumes that the chemist has access to L-prolinol with the correct stereochemistry to simplify the synthesis. Each step should be optimized for yield and purity, taking into consideration the specific reaction conditions such as temperature, solvent, and reaction time.
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