190714-53-5

Upstream product

• 75-26-3 isopropyl bromide 
• 488-17-5 3-methylbenzene-1,2-diol 
• 287117-34-4 1,2-diisopropoxy-3-methyl-benzene 
• 287117-33-3 2-isopropoxy-3-methyl-phenol 

Downstream Products

• 287117-34-4 1,2-diisopropoxy-3-methyl-benzene 
• 18102-31-3 2-methoxy-3-methylphenol 
• 287117-36-6 4-bromo-2-methoxy-3-methylphenol 
• 287117-37-7 1-bromo-4-isopropoxy-3-methoxy-2-methyl-benzene 
• 287117-31-1 2-bromo-5-hydroxy-4-methoxy-3-methylbenzaldehyde 
• 287117-38-8 2-bromo-5-isopropyloxy-4-methoxy-3-methylbenzaldehyde 
• 287117-39-9 5-bromo-2-isopropoxy-3-methoxy-4-methyl-benzaldehyde 
• 1258431-60-5 4-hydroxy-3-isopropoxy-5-methylbenzaldehyde 
• 287117-35-5 1-isopropoxy-2-methoxy-3-methyl-benzene 

Relevant academic research and scientific papers

Synthesis of (±)-phthalascidin 650 analogue: New synthetic route to (±)-phthalascidin 622

A synthesis of functionalized phenolic α-amino-alcohol (±)-13 as synthetic precursor of the catechol tetrahydroisoquinoline structure of phthalascidin 650 is disclosed. Starting from 3-methylcatechol 5, eight steps of synthesis give rise to the synthesis of phenolic α-amino-alcohol (±)-13 in 27% overall yield. This synthetic strategy involves the elaboration of fully functionalized aromatic aldehyde 8 and its transformation into a phenolic α-amino-alcohol (±)-13, through a Knoevenagel condensation, simultaneous reduction of nitroketene and ester functions and hydrogenolysis of the benzyl protecting group. The pentacycle (±)-18 was obtained after four additional steps. The Pictet-Spengler cyclisation between the phenolic α-amino-alcohol (±)-13 and N-protected α-amino-aldehyde 4 allowed to obtain (1,3′)-bis- tetrahydroisoquinoline 14 with N-methylated and N-Fmoc removed. The last step was a Swern oxidation for allowing an intramolecular condensation.

A concise route to 3-hydroxy-4-methoxy-5-methylbenzaldehyde derivative

3-Hydroxy-4-methoxy-5-methylbenzaldehyde derivative (1c) has been synthesized in 7 steps from 2,3-dihydroxytoluene (4). An isopropyl derivative has been used to protect a phenol during this transformation. The overall yield of 1c was 37%.