286936-08-1

Basic information

• Product Name: (2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one
• Synonyms: (2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one;(2S,3S,4aR,8R,8aR)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-6-one
• CAS NO: 286936-08-1
• Molecular Formula: C12H20O6
• Molecular Weight: 260.2836
• Product Categories: Aromatics, Heterocycles, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 286936-08-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 148-150 °C
• Boiling Point: 384.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Solubility: Chloroform, DCM
• PKA: 13.09±0.60(Predicted)
• CAS DataBase Reference: (2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one(286936-08-1)
• EPA Substance Registry System: (2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one(286936-08-1)

Safety Data

• Hazardous Substances Data: 286936-08-1(Hazardous Substances Data)

Usage

Description

(2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one is a complex organic compound characterized by its unique stereochemistry and structural features. It is a key intermediate in the synthesis of various biologically active molecules and has potential applications in the pharmaceutical and chemical industries due to its versatile chemical properties.

Uses

Used in Pharmaceutical Industry:
(2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one is used as an intermediate in the synthesis of (-)-Altenuene (A575740), a toxin isolated from the fungus Alternaria tenuis. (2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one has potential applications in the development of new drugs and therapeutic agents, particularly in the area of natural product-based drug discovery.
Used in Chemical Industry:
(2S,3S,4aR,8R,8aR)-Hexahydro-8-hydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6(5H)-one can be utilized as a building block for the synthesis of various complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structural features and versatile chemical properties make it a valuable component in the development of novel compounds with diverse applications.

Upstream product

• 286936-07-0 (2S,3S,4aR,5R,7S,8aR)-7-Hydroxymethyl-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-5,7-diol 
• 176798-26-8 (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 77-95-2 D-(-)-quinic acid 
• 431-03-8 dimethylglyoxal 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 286936-09-2 (2'S,3'S,4R,5R)-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-4,5-dihydroxycyclohex-2-en-1-one 
• 1313484-43-3 C₂₉H₃₈O₆Si 
• 1313484-30-8 C₃₀H₄₀O₆Si 
• 1313484-31-9 C₃₀H₄₂O₆Si 
• 1313484-44-4 C₃₀H₄₂O₆Si 
• 1313484-32-0 C₂₄H₃₂O₄Si 
• 1313484-33-1 C₃₀H₄₄O₇Si 
• 1313484-36-4 C₁₄H₂₆O₇ 
• 1313484-37-5 C₂₁H₃₆O₈ 
• 1313484-35-3 C₄₂H₇₄O₄Si₄ 
• 1313484-34-2 C₃₉H₅₆O₇Si 
• 1313484-45-5 C₂₃H₃₈O₇ 
• 1313484-38-6 C₂₁H₃₆O₈ 
• 1313484-46-6 C₃₀H₄₈O₈ 

Relevant articles and documents

Stereocontrolled Synthesis of (-)-Bactobolin A

A stereoselective synthesis of the ribosome-binding antitumor antibiotic (-)-bactobolin A is reported. The presented approach makes effective use of (-)-quinic acid as a chiral pool starting material and substrate stereocontrol to establish the five contiguous stereocenters of (-)-bactobolin A. The key steps of the synthesis include a stereoselective vinylogous aldol reaction to introduce the unusual dichloromethyl substituent, a completely diastereoselective rhodium(II)-catalyzed C-H amination reaction to set the configuration of the axial amine, and an intramolecular alkoxycarbonylation to build the bicyclic lactone framework. The developed synthetic route was used to prepare 90 mg of (-)-bactobolin A trifluoroacetate in 10% overall yield.

The synthesis of 2-oxyalkyl-cyclohex-2-enones, related to the bioactive natural products COTC and antheminone A, which possess anti-tumour properties

The syntheses of five novel 2-oxyalkyl-cyclohex-2-enones, structurally related to the natural products COTC and antheminone A, are described. The target structures were selected in order to probe the influence of several key structural parameters on in vi

Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties

The syntheses of three novel analogues of the naturally occurring cytotoxic agent COTC are described and the results of bioassays of the target compounds against two lung cancer cell lines are presented.