(1R,5S,6R)-rel-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid

Name: (1R,5S,6R)-rel-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid
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CAS No. 55780-88-6
Cat. No. CS-0036007
Purity≥95%
MDL No.None

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(1R,5S,6R)-rel-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid|CS-0036007

Structure of 55780-88-6

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General Information

CAS No. 55780-88-6
Cat. No. CS-0036007
Purity ≥95%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₈O₃
Molecular Weight 128.13
Synonym(s) (1R,5S,6s)-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid
SMILES C1[C@H]2[C@@H](CO1)[C@@H]2C(=O)O

Description

This bicyclic scaffold features a rigid, oxygen-bridged ring system with defined stereochemistry at the 1,5,6 positions. The carboxylic acid group provides a handle for derivatization, while the strained framework imparts unique conformational control. Ideal for probing steric and electronic effects in synthetic applications.

Application

(1R,5S,6R)-rel-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid serves as a rigid, conformationally constrained scaffold for medicinal and synthetic chemistry applications. Its bicyclic structure imparts defined stereochemistry and spatial rigidity, enabling precise control in ligand design and target engagement studies. The carboxylic acid functionality facilitates derivatization via amide bond formation or esterification, while the ether bridge enhances metabolic stability. This compound functions as a valuable building block in the synthesis of bioactive heterocycles and serves as a key structural motif in lead optimization campaigns requiring defined molecular topology.

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-P280-P302+P352

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Computational Chemistry Data

TPSA 46.53
LogP -0.0366
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Tetrahydropyran compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Fatty ring compounds Cyclopropane compounds

Key Words

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(1R,5S,6R)-rel-3-Oxabicyclo[3.1.0]hexane-6-carboxylic acid

CAS No. 55780-88-6

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