228997-09-9

Upstream product

• 99-10-5 3,5-Dihydroxybenzoic acid 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 228997-10-2 N,N-diethyl-3,5-bis(methoxymethoxy)benzamide 
• 1140194-84-8 3,5-bis(methoxymethoxy)-4-methylbenzoic acid 
• 926294-00-0 3,5-dihydroxy-N-(3-hydroxyphenyl)benzamide 
• 228997-25-9 (5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-<<(4-methoxyphenyl)methyl>thio>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 228997-23-7 (1R,3R)-6,8-bis(benzyloxy)-1-<(4-(benzyloxy)phenyl)methyl>-5-<<(4-methoxyphenyl)methyl>thio>-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester 
• 228997-24-8 (1R,3R)-6,8-bis(benzyloxy)-1-<<4-(benzyloxy)phenyl>methyl>-3-hydroxymethyl-5-<<(4-methoxyphenyl)methyl>thio>-1,2,3,4-tetrahydroisoquinoline 
• 228997-22-6 N-<<4-(benzyloxy)phenyl>acetyl>-3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>-D-phenylalanine methyl ester 
• 228997-26-0 (5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 
• 228997-18-0 (2S-trans)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine 
• 228997-19-1 (2S-cis)-2,5-dihydro-3,6-dimethoxy-5-<<3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>phenyl>methyl>-2-(1-methylethyl)pyrazine 
• 228997-20-4 3,5-bis(benzyloxy)-2-<<(4-methoxyphenyl)methyl>thio>-D-phenylalanine methyl ester 
• 228997-13-5 3,5-bis(benzyloxy)-N,N-diethyl-2<<(4-methoxyphenyl)methyl>thio>benzamide 
• 228997-14-6 3,5-bis(benzyloxy)-N,N-diethyl-2<<(4-methoxyphenyl)methyl>thio>benzenemethanamine 
• 228997-29-3 3,5-bis(benzyloxy)-1-(chloromethyl)-2-<<(4-methoxxyphenyl)methyl>thio>benzene 

Relevant academic research and scientific papers

Synthesis of 4′-ester analogs of resveratrol and their evaluation in malignant melanoma and pancreatic cell lines

4′-Ester analogs of the disease preventative agent resveratrol were synthesized and evaluated for their potential as anti-melanoma and pancreatic cancer agents. A decarbonylative Heck coupling was used to assemble the protected stilbene core structure. Th

Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative Heck couplings

Protected 3,5-hydroxy-benzoyl chlorides 3 were coupled with styrenes 4 to give hydroxylated stilbenes, analogs of resveratrol, an important antioxidant disease preventative agent isolated from grape skins and other dietary sources. Levulinate and chloroacetate protecting groups allowed for the selective production of mono- and di-acetate variations under palladium-N-heterocyclic carbene (NHC) catalyzed decarbonylative coupling conditions. Fluorinated analogs were also produced using Heck conditions with bromofluorobenzenes. Human HL-60 cell assays showed the 4′-acetoxy variant 11 to have improved activity (ED50 17 μM) relative to resveratrol (24 μM).

Synthetic studies on the starfish alkaloid imbricatine. A chiral synthesis of tri-O-methylimbricatine

A detailed account is given of the chiral synthesis of tri-O- methylimbricatine (3), the triO-methyl derivative of the structurally unique benzyltetrahydroisoquinoline alkaloid imbricatine (2) isolated from the starfish Dermasterias imbricata. The route begins with the asymmetric synthesis of the sulfur-containing D-phenylalanine derivative (R)-11a and includes its conversion into the cis-benzyltetrahydroisoquinoline moiety 26a possessing the thiol group and construction of the 5-arylthio-3-methyl-L- histidine portion. The correctness of the structure and absolute configuration proposed for imbricatine has been unequivocally confirmed as a result of the present synthesis.