16051-42-6

Basic information

• Product Name: (+/-)-threo-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid
• CAS NO: 16051-42-6
• Molecular Weight: 240.256
• Mol File: 16051-42-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+/-)-threo-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-threo-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid(16051-42-6)
• EPA Substance Registry System: (+/-)-threo-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid(16051-42-6)

Safety Data

• Hazardous Substances Data: 16051-42-6(Hazardous Substances Data)

Upstream product

• 16051-39-1 (+/-)-threo-(3,5-dihydroxy-2-methyphenyl)butan-2-ol (phenol B) 
• 100560-67-6 (+/-)-threo-3,4-dihydro-6,8-dimethoxy-3,4-dimethyl-1H-2-benzopyran-1-one 
• 92120-69-9 ethyl 2-ethyl-4,6-dimethoxybenzoate 
• 110087-19-9 (+/-)-threo-3,4-dihydro-6,8-dimethoxy-3,4-dimethyl-1H-2-benzopyran 
• 79755-60-5 (+/-)-threo-3-(3,5-dimethoxy-2-methyl-phenyl)-butan-2-ol 
• 110087-16-6 ethyl (+/-)-2,4-dimethoxy-6-(1-methyl-2-oxopropyl)benzoate 
• 110087-15-5 (+/-)-threo-2-(2-hydroxy-1-methylpropyl)-4,6-dimethoxybenzoate 
• 124-38-9 carbon dioxide 

Downstream Products

• 112245-92-8 L_g-threo-2-(3.5-dihydroxy-2-methyl-phenyl)-butanol-⁽³⁾ 
• 79755-69-4 5-((1S,2R)-2-Hydroxy-1-methyl-propyl)-4-methyl-benzene-1,3-diol 
• 518-75-2 (+/-)-threo-4,6-dihydro-8-hydroxy-3,4,5-trimrthyl-6-oxo-3H-2-benzopyran-7-carboxylic acid (citrinin) 
• 112245-93-9 2,6-dihydroxy-4-((1R,2S)-2-hydroxy-1-methyl-propyl)-3-methyl-benzoic acid 
• 163660-01-3 (1S,2R)-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid 

Relevant articles and documents

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A Diastereoselective Synthesis of the Polyketide Antibiotic Citrinin using Toluate Anion Chemistry

The diastereoselectivity of various synthetic approaches to (+/-)-threo-3-(3,5-dihydroxy-2-methylphenyl)butan-2-ol ('Phenol B') (4), based on reactions of benzyl anions with electrophiles, has been investigated.The anion (9) derived from ethyl 2,4-dimethoxy-6-ethylbenzoate reacted with acetaldehyde to give mainly an erythro-product isolated as the lactone (12); acetylation with acetyl chloride to give a ketone, followed by reduction, gave mainly the required threo-lactone (11).An alternative route was frustrated by decomposition of the benzyl anion derived from 3,4-dihydro-6,8-dimethoxy-3-methyl-1H-2-benzopyran-1-one (17).Reduction of the carbonyl group of the threo-lactone (11) to a methyl gave the dimethyl ether of 'Phenol B', which was converted into (+/-)-citrinin (1).