488703-60-2

Basic information

• Product Name: (1S,2S)-BOC-2-AMINOCYCLOHEXANE CARBOXYLIC ACID
• Synonyms: (1S,2S)-BOC-2-AMINOCYCLOHEXANE CARBOXYLIC ACID;(1S,2S)-BOC-ACHC;(1S,2S)-2-tert-Butoxycarbonylamino-cyclohexanecarboxylic acid;Cyclohexanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (1S,2S)-;(1S,2S)-2-((tert-Butoxycarbonyl)amino)cyclohexane-1-carboxylic acid;(1S,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexane-1-carboxylic acid
• CAS NO: 488703-60-2
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.3
• Mol File: 488703-60-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 396.7±31.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.95±0.28(Predicted)
• CAS DataBase Reference: (1S,2S)-BOC-2-AMINOCYCLOHEXANE CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-BOC-2-AMINOCYCLOHEXANE CARBOXYLIC ACID(488703-60-2)
• EPA Substance Registry System: (1S,2S)-BOC-2-AMINOCYCLOHEXANE CARBOXYLIC ACID(488703-60-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 488703-60-2(Hazardous Substances Data)

Usage

General Description

(1S,2S)-Boc-2-aminocyclohexane carboxylic acid is a chemical compound that belongs to the class of Boc-protected amino acids. It has a molecular formula of C11H19NO4 and a molecular weight of 229.27 g/mol. The compound is a carboxylic acid derivative that contains an amino group and a cyclohexane ring. The Boc (tert-butoxycarbonyl) protection group is commonly used in peptide synthesis to protect the amine group and prevent unwanted reactions. (1S,2S)-Boc-2-aminocyclohexane carboxylic acid is often utilized in the synthesis of peptides and pharmaceutical intermediates due to its stability and compatibility with the standard peptide coupling reagents and procedures.

Upstream product

• 488703-61-3 (1S)-trans-2-carbamoyl-cyclohexanecarboxylic acid 
• 610-10-6 (1S,2S)-cyclohexane-1,2-dicarboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 158414-45-0 (1S,2S)-(+)-2-aminocyclohexane-1-carboxylic acid hydrochloride 

Downstream Products

• 948915-87-5 C₂₃H₄₀N₃O₆ 
• 948915-88-6 C₃₃H₄₂N₃O₆ 
• 948915-89-7 C₁₈H₃₂N₃O₄ 
• 948915-95-5 C₂₂H₃₈N₃O₆ 
• 948915-90-0 C₃₀H₅₁N₄O₇ 
• 948915-96-6 C₂₉H₄₉N₄O₇ 
• 948915-91-1 C₃₇H₆₂N₅O₈ 
• 948915-97-7 C₃₆H₆₀N₅O₈ 
• 1032733-34-8 C₄₀H₆₃N₃O₁₂ 
• 1032733-35-9 C₄₂H₆₇N₃O₁₃ 
• 1032733-36-0 C₄₈H₇₁N₃O₁₄ 
• 1032733-37-1 C₃₀H₄₅N₃O₆ 
• 1032733-38-2 Boc-(1S,2S)-ACHC-(S)-β3-HAla-(1S,2S)-ACHC-OMe 
• 1032733-39-3 C₄₇H₇₄N₄O₁₃ 

Relevant articles and documents

Enantiomerically pure β-amino acids: A convenient access to both enantiomers of trans-2-aminocyclohexanecarboxylic acid

Enantiomerically pure trans-2-aminocyclohexanecarboxylic acid is an important building block for helical β-peptides. We report here that this amino acid can be obtained from trans-cyclohexane-1,2-dicarboxylic acid in good yield by a simple one-pot procedure comprising cyclization to the anhydride, amide formation with ammonia, and a subsequent Hofmann-type degradation with phenyliodine(III) bis(trifluoroacetate) (PIFA) as the oxidant. The N-Fmoc- and N-BOC-protected derivatives were obtained by treatment of the amino acid with Fmoc-OSu and BOC2O, respectively. The N-BOC derivative could be prepared in even better overall yield by a one-pot procedure leading directly from trans-cyclohexane-1,2-dicarboxylic acid to the N-BOC-protected amino acid. Both enantiomers of the starting trans-1,2-cyclohexanedicarboxylic acid can be obtained easily and in large quantities by separating commercially available racemic trans-1,2-cyclohexanedicarboxylic acid using either (R)- or (S)-1-phenethylamine. X-ray crystallography of the diastereomerically pure salt obtained from (R)-1-phenethylamine revealed that the configuration of the diacid component is (1R,2R), and not (1S,2S) as reported in the literature. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.