(S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Name: (S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 142335-42-0
Cat. No. CS-0108775
Purity≥95%
MDL No.MFCD00671683

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(S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid|CS-0108775

Structure of 142335-42-0

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General Information

CAS No. 142335-42-0
Cat. No. CS-0108775
Purity ≥95%
MDL No. MFCD00671683
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₉NO₅
Molecular Weight 293.32
Synonym(s) BOC-7-HYDROXY-TIC-OH
SMILES OC1=CC=C2C(CN(C(OC(C)(C)C)=O)[C@H](C(O)=O)C2)=C1

Description

This chiral tetrahydroisoquinoline derivative features a protected amine, a hydroxyl group, and a carboxylic acid—ideal for constructing complex alkaloid scaffolds. The tert-butoxycarbonyl group enables selective deprotection during peptide coupling or cyclization sequences. Designed for synthetic efficiency in medicinal chemistry applications.

Application

(S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid serves as a versatile chiral building block for the synthesis of substituted tetrahydroisoquinoline scaffolds. The protected amine and carboxylic acid functionalities enable orthogonal derivatization, while the phenolic hydroxyl group supports selective functionalization. Bench-stable and compatible with standard coupling and reduction protocols, it facilitates efficient access to bioactive analogs in medicinal chemistry campaigns.

Synthesis

Route1
- 142335-41-9
- ~88%
- In-stock
  
  142335-42-0
References
- Zhang, Yingjie; Fang, Hao; Feng, Jinhong; Jia, Yuping; Wang, Xuejian; Xu, Wenfang Journal of Medicinal Chemistry, 2011 , vol. 54, # 15 p. 5532 - 5539
Route2
- In-stock
  
  24424-99-5
- In-stock
  
  128502-56-7
- ~99%
- In-stock
  
  142335-42-0
References
- Page; McClory; Mischki; Schmidt; Butterworth; St-Onge; Labarre; Payza; Brown Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 2 p. 167 - 170
Route3
- 262616-16-0
- ~%
- In-stock
  
  142335-42-0
References
- EP1857444 A1, ; Page/Page column 60 ;

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 87.07
LogP 2.1386
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Phenol

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Tetrahydroisoquinoline compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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(S)-2-(tert-Butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

CAS No. 142335-42-0

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