83553-80-4

Basic information

• Product Name: 3,5-Di-O-acetylgallussaeuremethylester
• Synonyms: 3,5-Di-O-acetylgallussaeuremethylester
• CAS NO: 83553-80-4
• Molecular Weight: 268.223
• Mol File: 83553-80-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3,5-Di-O-acetylgallussaeuremethylester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Di-O-acetylgallussaeuremethylester(83553-80-4)
• EPA Substance Registry System: 3,5-Di-O-acetylgallussaeuremethylester(83553-80-4)

Safety Data

• Hazardous Substances Data: 83553-80-4(Hazardous Substances Data)

Upstream product

• 20189-90-6 3,4,5-triacetoxy-benzoic acid methyl ester 
• 99-24-1 methyl galloate 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 108-24-7 acetic anhydride 
• 102019-30-7 4-O-benzyl-3,5-diacetoxybenzoic acid methyl ester 

Downstream Products

• 84274-52-2 gallic acid 4-O-β-D-glucopyranoside 
• 80220-30-0 4-O-(6-O-Sulfo-β-D-glucopyranosyl)gallussaeure 
• 54186-43-5 N-(3-methoxyphenylethyl)-(3,5-dibenzyloxy-4-methoxyphenyl)acetamide 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 54186-42-4 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetic acid 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 24093-82-1 3,5-bis(benzyloxy)-4-methoxybenzyl chloride 
• 27229-56-7 [3,5-bis(benzyloxy)-4-methoxyphenyl]methanol 
• 54186-41-3 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 13089-97-9 methyl 3,5-diacetoxy-4-methoxy benzoate 
• 114103-31-0 3,5-Di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)gallussaeuremethylester 

Relevant articles and documents

Chemistry of opium alkaloids, 45. Improvements in the total synthesis of morphine

The chiral 1,2,3,4-tetrahydroisoquinoline intermediates in the Price and Beyerman routes to morphine, (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy- 1,2,3,4-tetrahydroisoquinoline (6) and (+)-(R)-1-(3,5-dibenzyloxy-4- methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (5), were prepared in high ee by ruthenium-catalyzed asymmetric transfer hydrogenation of the corresponding imine precursors (Noyori method). The yield of the key raw material in the Beyerman route, 3,5-dibenzyloxy-4-methoxyphenylacetric acid (1), starting from gallic acid methyl ester (7) was improved by a factor of 5 over previously described syntheses. Key steps in the new procedure are the selective formation of methyl 3,5-dihydroxy-4-methoxybenzoate (9) via the 3,5-diacetate and an improved benzylation of the hydroxyl groups in 9.

VOM RADIOAKTIVEN CONIFERIN ZUM MARKIERTEN TURGORIN

The first Periodic Leaf Movement Factor ("PLMF 1"), 4-O-(β-D-glucopyranosyl 6-sulfate)gallic acid (1), which is chemonastically active on Mimosa pudica L., and its (14)C-carboxyl-labelled analog were synthesized by Koenigs-Knorr reaction of a D-glucose derivative with a suitably blocked gallic acid to give 4-O-β-D-glucopyranosylgallic acid after deblocking.Regioselective sulfatation with sulfur trioxide-pyridine afforded 1.The (14)C-labelled analog was prepared via regioselective glucosylation of methyl galloate with 2,3,4,6-tetra-D-acetyl-α-D-glucopyranosyl bromide and subsequent sulfatation of the deblocked glucoside.