82534-75-6

Basic information

• Product Name: (3R,12aR)-3,6α,9β-Trimethyl-3β,12α-epoxy-3,4,5,5aα,6,7,8,8aα,9,10-decahydro-10α-ethoxypyrano[4,3-j]-1,2-benzodioxepin
• Synonyms: (3R,12aR)-3,6α,9β-Trimethyl-3β,12α-epoxy-3,4,5,5aα,6,7,8,8aα,9,10-decahydro-10α-ethoxypyrano[4,3-j]-1,2-benzodioxepin;(3R,5aα,8aα,12aR)-10α-Ethoxydecahydro-3,6α,9β-trimethyl-3β,12α-epoxypyrano[4,3-j]-1,2-benzodioxepin;(3R,5aS,6R,8aS,9R,10R,12R,12aR)-10-Ethoxydecahydro-3,6,9-triMethyl-3,12-epoxy -12H-pyrano[4,3-j]-1,2-benzodioxepin
• CAS NO: 82534-75-6
• Molecular Formula: C₁₇H₂₈O₅
• Molecular Weight: 312.40122
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 82534-75-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 372.4 °C at 760 mmHg
• Flash Point: 146 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 2.06E-05mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: (3R,12aR)-3,6α,9β-Trimethyl-3β,12α-epoxy-3,4,5,5aα,6,7,8,8aα,9,10-decahydro-10α-ethoxypyrano[4,3-j]-1,2-benzodioxepin(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,12aR)-3,6α,9β-Trimethyl-3β,12α-epoxy-3,4,5,5aα,6,7,8,8aα,9,10-decahydro-10α-ethoxypyrano[4,3-j]-1,2-benzodioxepin(82534-75-6)
• EPA Substance Registry System: (3R,12aR)-3,6α,9β-Trimethyl-3β,12α-epoxy-3,4,5,5aα,6,7,8,8aα,9,10-decahydro-10α-ethoxypyrano[4,3-j]-1,2-benzodioxepin(82534-75-6)

Safety Data

• Hazardous Substances Data: 82534-75-6(Hazardous Substances Data)

Usage

Uses

The diastereomer of Arteether, a potent antimalarial drug.

InChI:InChI=1/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14-,15-,16-,17-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 75887-54-6 artemotil 
• 81496-81-3 dihydroartesiminin 
• 71939-50-9 dihydroartemisinin 
• 71939-50-9 dihydroartemisinin 

Downstream Products

• 129371-40-0 (R)-2-((1S,4R)-4-Methyl-7-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl)-propionaldehyde 

Relevant articles and documents

One-pot green synthesis of β-artemether/arteether

An efficient one pot green synthesis of β-artemether/arteether from artemisinin has been developed using a sodium borohydride-cellulose sulfuric acid (CellSA) catalyst system. The green methodology is high yielding and the catalyst has good recyclability.

PREPARATIVE PROCESS FOR ETHER DERIVATIVE OF ARTEMISININ

The present invention relates to a process for synthesis of ether derivative of artemisinin by reducing artemisinin to dihydroartemisinin using a mixture of sodium borohydride and a dihydroxy compound, followed by etherification in presence of an acid catalyst and an alcohol.

An improved procedure for the synthesis of ethers of dihydroartemisinin

A simple and efficient method for the preparation of ethers (3a-f) of dihydroartemisinin (2) has been developed using chlorotrimethylsilane as a catalyst.