52144-91-9

Upstream product

• 186581-53-3 diazomethane 
• 28917-44-4 3,5-dibenzyloxylbenzoyl chloride 
• 100-44-7 benzyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 100-39-0 benzyl bromide 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 50513-72-9 (3,5-di-benzyloxy)benzoic acid benzyl ester 
• 28917-43-3 3,5-dibenzyloxybenzoic acid 
• 99-10-5 3,5-Dihydroxybenzoic acid 

Downstream Products

• 79762-35-9 methyl 2-(3,5-bis(benzyloxy)-2-formylphenyl)acetate 
• 28924-18-7 2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone 
• 65857-83-2 8,10-bis(benzyloxy)-11-hydroxy-3-methoxy-1-methylbenzoxanthen-12-one 
• 65900-57-4 1,3-bis(benzyloxy)-6-hydroxy-10-methoxy-8-methylbenzoxanthen-7-one 
• 65857-82-1 1,3-bis(benzyloxy)-6-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)-10-methoxy-8-methylbenzoxanthen-7-one 
• 65857-85-4 1,3-bis(benzyloxy)-10-methoxy-8-methylbenzoxanthen-5,6,7-trione 
• 33390-22-6 norbikaverin 
• 65857-80-9 1,3-bis(benzyloxy)-6,8-bis-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)naphthalene 
• 65857-81-0 1,3-bis(benzyloxy)-7-(2-benzyloxy-4-methoxy-6-methylbenzoyl)-6-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)-8-hydroxynaphthalene 
• 71741-19-0 1,3-bis(benzyloxy)-6-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)-8-hydroxynaphthalene 
• 71741-23-6 1-acetoxy-6,8-bis(benzyloxy)-3-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)naphthalene 
• 71741-20-3 1,3-bis(benzyloxy)-5-(2-benzyloxy-4-methoxy-6-methylbenzoyl)-8-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)-6-hydroxynaphthalene 
• 33390-21-5 bikaverin 
• 71741-18-9 6,8-Bis-benzyloxy-naphthalene-1,3-diol 

Relevant academic research and scientific papers

A facile preparation of α-aryl carboxylic acid via one-flow arndt-eistert synthesis

An efficient, one-flow Arndt-Eistert synthesis was demonstrated. A sequence of acid chloride formation-nucleophilic acyl substitution-Wolff rearrangement-nucleophilic addition was performed in a microflow system without isolating any intermediates, which

Solid-phase synthesis using (Allyloxy)carbonyl(Alloc) chemistry of a putative heptapeptide intermediate in vancomycin biosynthesis containing m-chloro-3-hydroxytyrosine

A convenient method for the solid-phase synthesis of putative linear heptapeptide intermediates in vancomycin biosynthesis is described, in particular, the heptapeptide D-Leu-Cyt-L-Asn-Hpg-Hpg-Cyt'-Dhpg (Cyt = (2R,3R)-m-chloro-3-hydroxytyrosine, Hpg = (R)-2-(p-hydroxyphenyl)glycine, Cyt' = (2S,3R)-m-chloro-3-hydroxytyrosine and Dhpg = (S)-2-(3,5-dihydroxyphenyl)glycine). The synthesis was performed on chlorotrityl resin and employed the (allyloxy)carbonyl protecting group for temporary N(α) protection during peptide-chain assembly.

A urinary metabolite of Δ1-tetrahydrocannabinol. The first synthesis of 4''-hydroxy-Δ1-tetrahydrocannabinol-7-oic acid labelled with deuterium

The first synthesis of 4''-hydroxy-Δ1-THC-7-oic acid, one of the three major metabolites of Δ1-THC identified in human urine is discussed. Methyl 4-(3,5-dihydroxyphenyl)butanoate (8) was prepared from 3,5-dihydroxybenzoic acid in an overall yield of 15%. 8 was condensed with a terpene synthon (9) under acidic conditions followed by hydrolysis and conversion of the 4''-carboxylic acid function to the corresponding methyl ketone using methyllithium. Reduction with NaBH4 afforded the secondary alcohol in the side-chain. Acetylation and removal of the 1,3-dithiane masking group gave the aldehyde in C-7-position which was further oxidized using NaClO2 followed by deacetylation to give the desired metabolite 14. The same procedure may be used for the synthesis of unlabelled 4''-hydroxy-Δ1-THC-7-oic acid.

Synthesis of Bikaverin

The total synthesis of bikaverin (1b) is described, from everninic acid (5) and 3,5-dihydrobenzoic acid (6).Dieckmann condensation of methyl 2-acetyl-3,5-bis(benzyloxy)phenylacetate (14), synthesised from (6), followed by treatment with protected everninic acid chloride (9) gave 1,3-bisbenzyloxy-6,8-bis(2-benzyloxy-4-methoxy-6-methylbenzyloxy)naphthalene (16).Photoinduced Fries rearrangement of (16) afforded 1,3-bis(benzyloxy)-7-(2-benzyloxy-4-methoxy-6-methylbenzoyl)-6-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)-8-hydroxynaphthalene (23).Ring closure of (23) with tetramethylammonium hydroxide in pyridine gave the angular benzoxanthene, 1,3-bis(benzyloxy-6-hydroxy)-10-methoxy-8-methylbenzoxanthen-7-one (25), which was oxidized with potassium dichromate to give the orthoquinone, 1,3-bis(benzyloxy)-10-methoxy-8-methylbenzoxanthen-5,6,7-trione (28).By a novel type of rearrangement, (28) was transformed into the linear benzoxanthen, 8,10-bis(benzyloxy)-3-methoxy-1-methylbenzoxanthen-6,11,12-trione (29) by treatment with silica gel.Oxidation and debenzylation of (29) with manganese dioxide in concentrated H2SO4 gave norbikaverin (1a).

Orally active bronchospasmolytic compounds and their preparation

Novel compounds are disclosed having useful activity as bronchodilators of improved longevity of action and reduced incidence of side effects. These compounds are described by the formula: EQU1 wherein R1 is a member of the class consisting of tertiary butyl and cyclobutyl, and R2 is a hydrogen or 2 to 5 carbon atom acyl radical, and pharmaceutically acceptable salts thereof. The activity of these compounds is compared to previously known bronchodilators such as 1-(3', 5'-dihydroxyphenyl)-2-(isopropylamino)-ethanol, having the common name orciprenaline, and 1-(3', 4'-dihydroxyphenyl-2-isoproplyamino-ethanol, having the common name isoprenaline.