tert-Butyl (S)-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)carbamate

Name: tert-Butyl (S)-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)carbamate
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CAS No. 66605-58-1
Cat. No. CS-0102971
Molecule weight357.44
Purity≥97%
MDL No.MFCD00235956

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tert-Butyl (S)-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)carbamate|CS-0102971

Structure of 66605-58-1

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General Information

CAS No. 66605-58-1
Cat. No. CS-0102971
Purity ≥97%
MDL No. MFCD00235956
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₂₇NO₄
Molecular Weight 357.44
Synonym(s) Boc-tyr(bzl)-OL
SMILES O=C(OC(C)(C)C)N[C@H](CO)CC1=CC=C(OCC2=CC=CC=C2)C=C1

Description

This chiral carbamate scaffold features a tert-butyl-protected hydroxyl group and a benzyloxy-substituted phenyl moiety, enabling selective functionalization in asymmetric synthesis. The S-configured stereocenter ensures high enantioselectivity in downstream transformations, while the bench-stable protecting group facilitates handling under standard conditions.

Application

tert-Butyl (S)-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)carbamate serves as a chiral building block for the synthesis of bioactive compounds, enabling stereoselective transformations via its protected hydroxyl and amine functionalities. Its bench-stable tert-butyl carbamate group facilitates straightforward deprotection under mild acidic conditions, while the benzyloxy-protected phenolic moiety allows orthogonal handling in complex molecule assembly. Functions effectively in standard coupling and functional group interconversion workflows.

Synthesis

Route1
- In-stock
  
  2130-96-3
- ~82%
- In-stock
  
  66605-58-1
References
- Mavridis, Ioannis; Kythreoti, Georgia; Koltsida, Konstantina; Vourloumis, Dionisios Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 4 p. 1329 - 1341
Route2
- 27513-44-6
- ~93%
- In-stock
  
  66605-58-1
References
- Richter, Jeremy M.; Whitefield, Brandon W.; Maimone, Thomas J.; Lin, David W.; Castroviejo, M. Pilar; Baran, Phil S. Journal of the American Chemical Society, 2007 , vol. 129, # 42 p. 12857 - 12869
Route3
- 92515-43-0
- ~89%
- In-stock
  
  66605-58-1
References
- Green, Rachel; Taylor, Piers J. M.; Bull, Steven D.; James, Tony D.; Mahon, Mary F.; Merritt, Andy T. Tetrahedron Asymmetry, 2003 , vol. 14, # 17 p. 2619 - 2623

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 67.79
LogP 3.6937
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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tert-Butyl (S)-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)carbamate

CAS No. 66605-58-1

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