tert-Butyl ((1R,2R)-2-hydroxycyclohexyl)carbamate

Name: tert-Butyl ((1R,2R)-2-hydroxycyclohexyl)carbamate
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CAS No. 155975-19-2
Cat. No. CS-0058568
Purity≥95%
MDL No.MFCD11656036

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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tert-Butyl ((1R,2R)-2-hydroxycyclohexyl)carbamate|CS-0058568

Structure of 155975-19-2

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General Information

CAS No. 155975-19-2
Cat. No. CS-0058568
Purity ≥95%
MDL No. MFCD11656036
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₂₁NO₃
Molecular Weight 215.29
Synonym(s) (1R,2R)-trans-N-Boc-2-aminocyclohexanol
SMILES O[C@H]1[C@H](NC(OC(C)(C)C)=O)CCCC1

Description

tert-Butyl ((1R,2R)-2-hydroxycyclohexyl)carbamate is a chiral auxiliary featuring a rigid cyclohexane scaffold with a stereodefined hydroxyl group and a bench-stable carbamate protecting group. This configuration enables selective functionalization in asymmetric synthesis, particularly in the installation of stereocenters via dihydroxylation or oxidation protocols. The protected alcohol remains inert under many reaction conditions while allowing controlled deprotection post-functionalization.

Application

tert-Butyl ((1R,2R)-2-hydroxycyclohexyl)carbamate serves as a stereochemically defined chiral building block for cyclohexane-based scaffolds. The protected amine and secondary alcohol functionalities enable orthogonal derivatization in synthetic sequences. Its bench-stable nature and compatibility with standard coupling and reduction protocols facilitate efficient access to complex cyclic architectures. Functions effectively in asymmetric synthesis and medicinal chemistry campaigns requiring rigid, stereoregular frameworks.

Synthesis

Route1
- 115586-44-2
- ~%
- In-stock
  
  155975-19-2
References
- Govindaraju; Gonnade, Rajesh G.; Bhadbhade, Mohan M.; Kumar, Vaijayanti A.; Ganesh, Krishna N. Organic Letters, 2003 , vol. 5, # 17 p. 3013 - 3016

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 58.56
LogP 1.8146
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Fatty ring compounds Cyclohexane compounds

Key Words

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tert-Butyl ((1R,2R)-2-hydroxycyclohexyl)carbamate

CAS No. 155975-19-2

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