tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Name: tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 114676-67-4
Cat. No. CS-0047100
Purity≥98%
MDL No.None

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tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate|CS-0047100

Structure of 114676-67-4

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General Information

CAS No. 114676-67-4
Cat. No. CS-0047100
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₃₃NO₄Si
Molecular Weight 331.52
Synonym(s) 4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid
SMILES O=C(N1[C@@H](C[C@H](C1)O[Si](C)(C(C)(C)C)C)CO)OC(C)(C)C

Description

tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate features a stereodefined pyrrolidine core with orthogonal protection: a silyl ether at C4 and a hydroxymethyl group at C2. This configuration enables selective functionalization in complex molecule synthesis. The tert-butyldimethylsilyl moiety offers robust stability under standard conditions while permitting late-stage deprotection.

Application

tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate serves as a stereochemically defined pyrrolidine building block with orthogonal protection. The silyl ether enables selective deprotection in the presence of other functional groups, while the hydroxymethyl moiety supports further derivatization. Its bench-stable nature and compatibility with standard coupling and reduction protocols facilitate efficient access to complex heterocyclic scaffolds in medicinal chemistry and natural product synthesis.

Synthesis

Route1
- In-stock
  
  114676-91-4
- ~95%
- In-stock
  
  114676-67-4
References
- Elsohly, Adel M.; Wespe, Daniel A.; Poore, Tyler J.; Snyder, Scott A. Angewandte Chemie - International Edition, 2013 , vol. 52, # 22 p. 5789 - 5794 Angew. Chem., 2013 , vol. 125, # 22 p. 5901 - 5906,7
Route2
- 753014-18-5
- ~93%
- In-stock
  
  114676-67-4
References
- APPLIED RESEARCH SYSTEMS ARS HOLDING N.V. Patent: WO2004/76407 A2, 2004 ; Location in patent: Page 27-29 ; WO 2004/076407 A2
Route3
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  114676-67-4
References
- Fujisawa Pharmaceutical Co., Ltd. Patent: US4822787 A1, 1989 ;

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 59
LogP 3.3785
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Functional Group Organosilicon compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

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tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

CAS No. 114676-67-4

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