tert-Butyl cis-3-hydroxycyclobutane-1-carboxylate

Name: tert-Butyl cis-3-hydroxycyclobutane-1-carboxylate
Brand: ChemScene
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CAS No. 939768-64-6
Cat. No. CS-0159501
Purity≥95%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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tert-Butyl cis-3-hydroxycyclobutane-1-carboxylate|CS-0159501

Structure of 939768-64-6

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General Information

CAS No. 939768-64-6
Cat. No. CS-0159501
Purity ≥95%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₆O₃
Molecular Weight 172.22
Synonym(s) Tert-butyl 3-hydroxycyclobutane-1-carboxylate
SMILES O=C([C@H]1C[C@@H](O)C1)OC(C)(C)C

Description

tert-Butyl cis-3-hydroxycyclobutane-1-carboxylate features a strained cyclobutane core with a stereochemically defined hydroxyl group and a bench-stable tert-butyl ester. This configuration enables direct incorporation into complex molecular architectures, where the hydroxyl moiety serves as a handle for selective derivatization. The cis arrangement ensures predictable conformational behavior in synthetic sequences.

Application

tert-Butyl cis-3-hydroxycyclobutane-1-carboxylate serves as a versatile chiral building block in synthetic organic chemistry, enabling stereoselective functionalization at the C3 hydroxyl position. The cyclobutane core provides conformational rigidity beneficial for medicinal chemistry applications, while the tert-butyl ester offers bench stability and facile deprotection under mild acidic conditions. Its well-defined stereochemistry supports predictable reactivity in coupling, oxidation, and cyclization processes relevant to heterocyclic and natural product synthesis.

Synthesis

Route1
- In-stock
  
  145549-76-4
- ~72%
- In-stock
  
  939768-64-6
References
- ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R. Patent: WO2011/71570 A1, 2011 ; Location in patent: Page/Page column 162 ;
Route2
- In-stock
  
  145549-76-4
- ~%
- In-stock
  
  939768-64-6
- 1311158-43-6
References
- Lukin, Kirill; Kishore, Vimal; Gordon, Thomas Organic Process Research and Development, 2013 , vol. 17, # 4 p. 666 - 671

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 46.53
LogP 1.099
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

Key Words

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tert-Butyl cis-3-hydroxycyclobutane-1-carboxylate

CAS No. 939768-64-6

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