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CS-W001157 4
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(R)-tert-butyl (1-hydroxybut-3-en-2-yl)carbamate

  • CAS No. 89985-86-4

  • Cat. No. CS-W000577
  • Molecule weight187.24
  • Purity≥98%
  • MDL No.MFCD19688626

*For research and further manufacturing use only, not for direct human use.

(R)-tert-butyl (1-hydroxybut-3-en-2-yl)carbamate|CS-W000577

Structure of 89985-86-4

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General Information

  • CAS No. 89985-86-4
  • Cat. No. CS-W000577
  • Purity ≥98%
  • MDL No. MFCD19688626
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₇NO₃
  • Molecular Weight 187.24
  • Synonym(s) tert-Butyl [(1R)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate
  • SMILES CC(C)(C)OC(=O)N[C@@H](CO)C=C

Description

(R)-tert-Butyl (1-hydroxybut-3-en-2-yl)carbamate features a chiral allylic alcohol scaffold with a bench-stable carbamate protecting group. This configuration enables stereoselective transformations in asymmetric synthesis, particularly in the construction of complex oxygenated intermediates. The pendant hydroxyl and alkene functionalities support downstream functionalization via oxidation, conjugate addition, or metal-catalyzed coupling reactions.

Application

(R)-tert-Butyl (1-hydroxybut-3-en-2-yl)carbamate serves as a versatile chiral building block for the synthesis of functionalized amino alcohols and heterocyclic scaffolds. Its pendant hydroxyl and enolizable olefin enable sequential transformations, including dihydroxylation, epoxidation, and palladium-catalyzed coupling reactions. The Boc group provides excellent stability during synthetic manipulations and can be selectively removed under mild acidic conditions. This compound facilitates the construction of complex intermediates in medicinal chemistry campaigns requiring stereocontrolled access to β-hydroxyamino acid derivatives.

Safety Information

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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

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Computational Chemistry Data

  • TPSA   58.56
  • LogP   1.058
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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