1225609-04-0

Basic information

• Product Name: (2S,5S,6S)-methyl 6-(3-(benzyloxy)-5-bromophenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate
• Synonyms: (2S,5S,6S)-methyl 6-(3-(benzyloxy)-5-bromophenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate
• CAS NO: 1225609-04-0
• Molecular Weight: 417.299
• Mol File: 1225609-04-0.mol

Chemical Properties

• CAS DataBase Reference: (2S,5S,6S)-methyl 6-(3-(benzyloxy)-5-bromophenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S,6S)-methyl 6-(3-(benzyloxy)-5-bromophenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate(1225609-04-0)
• EPA Substance Registry System: (2S,5S,6S)-methyl 6-(3-(benzyloxy)-5-bromophenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate(1225609-04-0)

Safety Data

• Hazardous Substances Data: 1225609-04-0(Hazardous Substances Data)

Downstream Products

• 1225609-84-6 C₂₁H₂₃BrO₅ 
• 1225609-07-3 (2S,3S,5S,6S)-methyl 6-(3-(benzyloxy)-5-bromophenyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-carboxylate 

Relevant articles and documents

Synthesis of reblastatin, autolytimycin, and non-benzoquinone analogues: Potent inhibitors of heat shock protein 90

A full account of an asymmetric synthesis of reblastatin (1) and the first total synthesis of autolytimycin (2) and related structural compounds is described. The syntheses expand the utility of a highly regio- and diastereoselective hydrometalation aldehyde addition sequence to assemble the fully functionalized ansa chain of the natural products. Also documented is an intramolecular copper-mediated amidation reaction to close the 19-membered macrolactams. The amidation reaction was also employed for the generation of structural derivatives (6-9) of phenolic ansamycins. Ansamycin natural products and selected structural analogues were evaluated in a competitive binding assay to breast cancer cell lysate and a cytotoxicity assay. Both reblastatin (1) and autolytimycin (2) were shown to bind the heat shock protein 90 with enhanced binding activity (～25 nM) than 17-allylamino-17-demethoxygeldanamycin (17-AAG, 4), a geldanamycin (3) derivative currently under evaluation for treatment of cancer (～100 nM).