16051-39-1

Basic information

• Product Name: (+/-)-threo-(3,5-dihydroxy-2-methyphenyl)butan-2-ol (phenol B)
• CAS NO: 16051-39-1
• Molecular Weight: 196.246
• Mol File: 16051-39-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+/-)-threo-(3,5-dihydroxy-2-methyphenyl)butan-2-ol (phenol B)(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-threo-(3,5-dihydroxy-2-methyphenyl)butan-2-ol (phenol B)(16051-39-1)
• EPA Substance Registry System: (+/-)-threo-(3,5-dihydroxy-2-methyphenyl)butan-2-ol (phenol B)(16051-39-1)

Safety Data

• Hazardous Substances Data: 16051-39-1(Hazardous Substances Data)

Upstream product

• 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 

Downstream Products

• 16051-42-6 (+/-)-threo-2,6-dihydroxy-4-(2-hydroxy-1-methylpropyl)-3-methylbenzoic acid 
• 81633-93-4 5-ethyl-4-methyl-resorcinol 
• 518-75-2 (+/-)-threo-4,6-dihydro-8-hydroxy-3,4,5-trimrthyl-6-oxo-3H-2-benzopyran-7-carboxylic acid (citrinin) 

Relevant articles and documents

Enantioselective Synthesis of the Polyketide Antibiotic (3R,4S)-(-)-Citrinin

The fungal metabolite (-)-citrinin (1) was synthesized for the first time.Reaction of the Grignard reagent of 2,4-bis(benzyloxy)-6-bromotoluene (3) with (2S)-trans-(-)-2,3-dimethyloxirane (6) in the presence of 1,5-cyclooctadienecopper(I) chloride as catalyst leads to the formation of (2S,3S)-(-)-7 with erythro configuration.Compound (-)-7 could be transformed into (2R,3S)-(-)-9 with threo configuration via the formate (1R,2S)-(+)-8 by a Mitsunobu reaction.Reaction of the Grignard reagent of 3 with the achiral cis-2,3-dimethyl-oxirane yielded directly (+/-)-9.The starting material 3 was readily available from 1,3-bis(benzyloxy)-5-bromobenzene (4).Formylation of 4 furnished the aldehyde 5 which could be reduced to 3 with borane.Hydrogenolysis of the benzyl ether groups in (-)-9 gave (-)-2 with threo configuration.The remaining steps to produce citrinin from (-)-2 required carboxylation to 11, formylation and in situ ring closure with ethyl orthoformate to produce the required quinomethide structure.Application of the same reactions to (+/-)-9 and (+/-)-2 afforded (+/-)-citrinin in 40percent overall yield. - Key Words: Citrinin, (3R,4S)-(-)- / 2,3-Dimethyloxirane, trans-(-)- and cis- / Synthesis of erythro- and threo-3-arylbutan-2-ols