110716-78-4

Basic information

• Product Name: (1R,2R)-trans-2-azidocyclohexanol
• Synonyms: (1R,2R)-trans-2-azidocyclohexanol
• CAS NO: 110716-78-4
• Molecular Weight: 141.173
• Mol File: 110716-78-4.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: (1R,2R)-trans-2-azidocyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-trans-2-azidocyclohexanol(110716-78-4)
• EPA Substance Registry System: (1R,2R)-trans-2-azidocyclohexanol(110716-78-4)

Safety Data

• Hazardous Substances Data: 110716-78-4(Hazardous Substances Data)

Upstream product

• 260260-97-7 (+)-(1R,2R)-2-azidocyclohexyl acetate 
• 108-05-4 vinyl acetate 
• 13374-31-7 (1R,2R)-trans-2-aminocyclohexanol hydrochloride 
• 123-62-6 propionic acid anhydride 
• 286-20-4 cyclohexane-1,2-epoxide 

Downstream Products

• 931-15-7 (1R,2R)-2-aminocyclohexanol 
• 189071-51-0 {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester 
• 178272-06-5 (4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid [(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-amide 
• 178272-07-6 {(4aR,6R,8R,8aR)-6-Methoxy-2-phenyl-6-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid methyl ester 
• 182265-23-2 N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-succinamic acid benzyl ester 
• 182265-22-1 4-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propylcarbamoyl}-butyric acid benzyl ester 
• 178272-03-2 (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester 
• 1439909-20-2 (1R,2R)-2-ethoxycyclohexanamine 
• 1439905-65-3 4-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-2-((1R,2R)-2-ethoxycyclohexylamino)pyrimidin-5-carboxamide 
• 1439909-19-9 C₈H₁₅N₃O 

Relevant articles and documents

MCM-41 bound dibenzo-18-crown-6 ether: a recoverable phase-transfer nano catalyst for smooth and regioselective conversion of oxiranes to β-azidohydrins and β-cyanohydrins in water

A new organic-inorganic hybrid nanocomposite was prepared by immobilizing dibenzo-18-crown-6 onto covalently linked amine functionalized mesoporous MCM-41 via a simple post-synthesis method. The heterogeneous hybrid nanocomposite was characterized by TEM,

A new chiral titanium species for the ring opening reactions of meso epoxides

The synthesis of a new chiral ligand 1 based on the conformationally defined 1,7-dioxaspiro[5.5]undecane ring system is reported. Generation of the corresponding ligand 1-Ti(OiPr)4 complex as a catalyst and its use in the enantioselective ring

Multigram-scale enzymatic kinetic resolution of trans-2-azidocyclohexyl acetate and chiral reversed-phase HPLC analysis of trans-2-azidocyclohexanol

Lipase-catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram-scale hydrolytic kinetic resolution of trans-2-azidocyclohexyl acetate using Pseudomonas cepacia lipase immobilized on Immobead support. We investigated several parameters of the preparative-scale process: temperature, organic co-solvent, and the influence of calcium ions. Moreover, we have developed an efficient fluorenylmethyloxycarbonyl chloride (Fmoc-Cl) derivatization protocol for 2-azidocyclohexanol, which enabled chiral reversed-phase high-performance liquid chromatography (RP-HPLC) determination of enantiomeric excess.

HheG, a halohydrin dehalogenase with activity on cyclic epoxides

Halohydrin dehalogenases (HHDHs) are of biotechnological interest due to their promiscuous epoxide ring-opening activity with a set of negatively charged nucleophiles, enabling the formation of C-C, C-N, or C-O bonds. The recent discovery of HHDH-specific sequence motifs aided the identification of a large number of halohydrin dehalogenases from public sequence databases, enlarging the biocatalytic toolbox substantially. During the characterization of 17 representatives of these phylogenetically diverse enzymes, one HHDH, namely HheG from Ilumatobacter coccineus, was identified to convert cyclic epoxide substrates. The enzyme exhibits significant activity in the azidolysis of cyclohexene oxide and limonene oxide with turnover numbers of 7.8 and 44 s-1, respectively. As observed for other HHDHs, the cyanide-mediated epoxide ring-opening proceeded with lower rates. Wild-type HheG displays modest enantioselectivity, as the resulting azido- and cyanoalcohols of cyclohexene oxide ring-opening were obtained in 40% enantiomeric excess. These biocatalytic findings were further complemented by the crystal structure of the enzyme refined to 2.3 ?. Analysis of HheG's structure revealed a large open cleft harboring the active site. This is in sharp contrast to other known HHDH structures and aids in explaining the special substrate scope of HheG.