158585-09-2

Basic information

• Product Name: benzyl 4-bromo-3,5-bis(benzyloxy)benzoate
• Synonyms: benzyl 4-bromo-3,5-bis(benzyloxy)benzoate
• CAS NO: 158585-09-2
• Molecular Weight: 503.392
• Mol File: 158585-09-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: benzyl 4-bromo-3,5-bis(benzyloxy)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 4-bromo-3,5-bis(benzyloxy)benzoate(158585-09-2)
• EPA Substance Registry System: benzyl 4-bromo-3,5-bis(benzyloxy)benzoate(158585-09-2)

Safety Data

• Hazardous Substances Data: 158585-09-2(Hazardous Substances Data)

Upstream product

• 16534-12-6 3,5-dihydroxy-4-bromobenzoic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 1012334-99-4 C₂₂H₂₈O₅ 
• 955886-14-3 tert-butyl 3,5-bis(benzyloxy)-4-((2-methyloxiran-2-yl)methyl)benzoate 
• 955886-13-2 tert-butyl 3,5-bis(benzyloxy)-4-(2-methylallyl)benzoate 
• 1254733-82-8 benzyl 2,6-bis(benzyloxy)-4'-fluorobiphenyl-4-carboxylate 

Relevant articles and documents

Total Synthesis of 3-Oxo- and 3β-Hydroxytauranin via Negishi Coupling of a Bis(ortho-oxy)-Functionalized Benzyl Chloride

The first asymmetric synthesis of the sesquiterpene quinones 3-oxo- and 3β-hydroxytauranin (1, 2) was achieved and the originally proposed structure of 3α-hydroxytauranin was revised. The protected benzyl chloride 5 was obtained in six steps starting from 4-bromo-3,5-dihydroxybenzoic acid (8) via a highly scalable approach. The troublesome Negishi coupling of the benzyl chloride 5 with alkenyldimethylalane 6 was optimized to furnish all-trans-farnesylarene 14 in very good yield. This prenylated arene was transformed in six additional steps to 3β-hydroxytauranin (2). Finally, a new convenient access to propargylated terpenes without using dry cryogenic ammonia and gaseous allene or propyne is described. The first total synthesis of the sesquiterpene quinones 3-oxo- and 3β-hydroxytauranin (2) was achieved and the originally proposed structure of 3α-hydroxytauranin was revised. The key step of the synthesis is the Negishi coupling of the bis(ortho-oxy)-functionalized benzyl chloride 5 with the alkenyldimethylalane 6.

SUBSTITUTED SPIROCYCLIC AMINES USEFUL AS ANTIDIABETIC COMPOUNDS

Substituted spirocyclic amines of structural formula I are selective antagonists of the somatostatin subtype receptor 5 (SSTR5) and are useful for the treatment, control or prevention of disorders responsive to antagonism of SSTR5, such as Type 2 diabetes, insulin resistance, lipid disorders, obesity, atherosclerosis, metabolic syndrome, depression, and anxiety.

Total Synthesis of Balanol and Designed Analogues

The total synthesis of balanol, a potent protein kinase C inhibitor isolated from the fungus Verticillium balanoides, is described.The hexahydroazepine fragment was prepared from D-serine through a sequence of reactions including the diastereoselective allylboration of a derived amino aldehyde and a base-induced 7-exo-tet ring closure as key steps.The benzophenone fragment was secured through the initial coupling of the two functionalised aromatic components through an ester linkage, followed by intramolecular nucleophilic attack of an aryl lithium derivative to form the desired ketone bridge.After coupling of the two balanol domains, the adoption of benzyl-derived protecting groups for the latent functionalities then allowed the liberation of balanol in a single step by catalytic hydrogenolysis.Finally, the newly developed synthetic strategy was applied to the synthesis of a variety of designed balanol analogues for biological evaluation. - Keywords: antitumor agents, balanol, enzyme inhibitor, natural product, total synthesis