176798-26-8

Basic information

• Product Name: (2S,3S,4aR,6S,8R,8aR)-Octahydro-6,8-dihydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6-carboxylic Acid Methyl Ester
• Synonyms: (2S,3S,4aR,6S,8R,8aR)-Octahydro-6,8-dihydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6-carboxylic Acid Methyl Ester;KCOAKJZBIWMLGL-JZJCQVGJSA-N
• CAS NO: 176798-26-8
• Molecular Formula: C₁₄H₂₄O₈
• Molecular Weight: 320.33556
• Product Categories: Aromatics, Heterocycles, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 176798-26-8.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• Solubility: Chloroform, DCM
• CAS DataBase Reference: (2S,3S,4aR,6S,8R,8aR)-Octahydro-6,8-dihydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6-carboxylic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4aR,6S,8R,8aR)-Octahydro-6,8-dihydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6-carboxylic Acid Methyl Ester(176798-26-8)
• EPA Substance Registry System: (2S,3S,4aR,6S,8R,8aR)-Octahydro-6,8-dihydroxy-2,3-diMethoxy-2,3-diMethyl-1,4-benzodioxin-6-carboxylic Acid Methyl Ester(176798-26-8)

Safety Data

• Hazardous Substances Data: 176798-26-8(Hazardous Substances Data)

Usage

Uses

(2S,3S,4aR,6S,8R,8aR)-Octahydro-6,8-dihydroxy-2,3-dimethoxy-2,3-dimethyl-1,4-benzodioxin-6-carboxylic Acid Methyl Ester is an intermediate in the synthesis of (-)-Altenuene (A575740), a toxin isolated from the fungus Alternaria tenuis.

Upstream product

• 191916-39-9 methyl (-)-quinate 
• 176798-33-7 2,2,3,3-tetramethoxybutane 
• 77-95-2 D-(-)-quinic acid 
• 431-03-8 dimethylglyoxal 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 97373-88-1 methyl (1R,3R,4S,5R)-1,5-dihydroxy-3,4-(isopropylidenedioxy)cyclohexane-1-carboxylate 
• 183474-88-6 methyl (1S,4S,5R)-1-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohexan-1-carboxylate 
• 78-98-8 2-oxopropanal 

Downstream Products

• 1246371-03-8 (1S, 3R, 4R, 5S)-5-(But-3'-enyl)-1,3,4,-trihydroxy-cyclohexanecarboxylic acid methyl ester 
• 1246371-04-9 (1S,3R,4R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsilyl)oxy]-1,4-dihydroxy-cyclohexanecarboxylic acid methyl ester 
• 1246371-06-1 (1S,3R,5S)-5-but-3-enyl-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxo-cyclohexanecarboxylic acid methyl ester 
• 1246371-08-3 (1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester 
• 1246370-95-5 3β,25-dihydroxy-19-norvitamin D3 
• 1246370-93-3 3β,25-dihydroxy-19-norvitamin D3 
• 1384545-88-3 C₂₇H₃₆O₁₁ 
• 1384545-92-9 C₄₀H₄₈O₁₄ 
• 1384545-90-7 C₄₄H₅₂O₁₄ 
• 1384545-94-1 C₄₂H₅₀O₁₄ 
• 1384545-96-3 C₄₂H₅₀O₁₄ 
• 1384546-04-6 methyl 3-feruloyl-muco-quinate 
• 1384546-08-0 methyl 1,3-di-O-feruloyl-muco-quinate 
• 1384546-02-4 methyl 3-O-caffeoyl-muco-quinate 

Relevant articles and documents

Lithium enolates from a (-)-quinic acid-derived cyclohexanone with a β-alkoxy leaving group: Regioselective preparation and evaluation of enolate stability towards β-elimination

Deprotonation of a (-)-quinic acid-derived ketone {(2S,3S,4aR,8R,8aS)-8- [(tert-butyl(dimethyl)silyl)oxy]-2,3-dimethoxy-2,3-dimethylhexahydro-1, 4-benzodioxin-6(5H)-one} using lithium hexamethyldisilazide (LHMDS) at -78°C gave one regioisomeric enolate. The regiocontrol is governed by the axial β-silyloxy substituent and the resulting lithium enolate is stable towards β-elimination at temperatures up to -40°C. It was found that the axial β-silyloxy group could be conveniently eliminated using 2.1equiv of LHMDS at 0°C for 1h and that an equatorial β-alkoxy group was much more resistant to β-elimination. A chiral lithium amide base was used to overturn the inherent regioselectivity of ketone deprotonation with LHMDS.

Dehydration of quinate derivatives: Synthesis of a difluoromethylene homologue of shikimic acid

An optimised procedure for the conversion of a quinate to shikimate structure has been developed using Martin's Sulfurane {Ph2S[OC(CF3)2Ph]2}. This protocol has been exploited in the synthesis of a novel difluor

(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid: The fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases

The fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases has been prepared from naturally occuring (-)-quinic acid over seven steps and has been shown to be the most potent inhibitor reported to date of the type

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (?)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-O-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure.

Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

We report a bio-inspired, strain driven epimerization of trans-ketals to cis-ketals through an enolate intermediate. Swern oxidation of a hydroxyl group adjacent to a trans-ketal effects both oxidation and its epimerization to cis-ketal. This novel and general strategy allows inversion of up to three contiguous stereocenters and has been illustrated by the synthesis of several unnatural/rare isomers of carbohydrates/cyclitols from their naturally abundant isomers. This journal is the Partner Organisations 2014.