310396-80-6

Upstream product

• 105192-33-4 6-<(4-methoxyphenyl)methoxy>hexan-1-ol 
• 4286-55-9 1-bromo-6-hexanol 
• 350848-02-1 2-[(4-methoxybenzyl)oxy]-3-nitropyridine 
• 629-11-8 1,6-hexanediol 
• 824-94-2 p-methoxybenzyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 258842-65-8 {3,5-bis-[6-(4-methoxy-benzyloxy)-hexyloxy]-phenyl}-methanol 
• 258842-66-9 malonic acid mono-{3,5-bis-[6-(4-methoxy-benzyloxy)-hexyloxy]-benzyl} ester 
• 258842-67-0 malonic acid 3,5-bis-[6-(4-methoxy-benzyloxy)-hexyloxy]-benzyl ester tert-butoxycarbonylmethyl ester 
• 322765-07-1 methyl (5S)-5-methoxymethoxy-12-p-methoxybenzyloxydodecanoate 
• 322765-08-2 (5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one 
• 324024-12-6 (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester 

Relevant academic research and scientific papers

Preparation of Alkyl Ethers with Diallyltriazinedione-Type Alkylating Agents (ATTACKs-R) Under Acid Catalysis

Diallyltriazinedione-type acid-catalyzed alkylating agents (ATTACKs-R) with 10 different alkyl groups (R), including benzyl, substituted benzyl, allyl, and methyl groups were synthesized. The palladium-catalyzed intramolecular O-to-N allylic rearrangement of 2,4-bis(allyloxy)-6-chloro-1,3,5-triazine was developed to introduce various alkoxy groups into the N,N′-dialkylated triazinedione skeleton. O-Alkylation of alcohols with ATTACKs-R was carried out in 1,4-dioxane in the presence of 2,6-di-tert-butylpyridinium trifluoromethanesulfonate or trifluoromethanesulfonic acid as a catalyst. Six selected ATTACKs-R bearing benzylic R groups were employed to prepare alkyl ethers from primary, secondary, and tertiary alcohols. The reactions of ATTACKs-R bearing an o-nitro-substituted benzyl group tended to afford low yields. Comparison of four different triazinedione-based benzylating reagents suggested that the N,N′-substituents affected the reactivity.

Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell

Electrochemical deprotection of p-methoxybenzyl (PMB) ethers was performed in an undivided electrochemical flow reactor in MeOH solution, leading to the unmasked alcohol and p-methoxybenzaldehyde dimethyl acetal as a byproduct. The electrochemical method removes the need for chemical oxidants, and added electrolyte (BF4NEt4) can be recovered and reused. The method was applied to 17 substrates with high conversions in a single pass, yields up to 92%, and up to 7.5 g h-1 productivity. The PMB protecting group was also selectively removed in the presence of some other common alcohol protecting groups.

Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers

Two different mixture synthesis routes have been used to make the four stereoisomers of petrocortyne A. A first quick and dirty route provided a mixture of the four isomers in nonselective fashion. Mosher and 2-naphthylmethoxyacetic acid (NMA) ester methods were developed to identify the components, and the mixture was partially resolved on analytical chiral HPLC to give the two pure enantiomers of petrocortyne A and the racemate of its diastereomer. A second fluorous mixture synthesis produced all four isomers of petrocortyne A in individual pure form. Comparison of spectra of Mosher derivatives of the synthetic isomers with two supposedly different natural products showed that both natural samples were instead identical and had the (3S,14S) configuration. Likewise, petrocortynes B, D, and F-H are (3S,14S) and petrocortyne D is (3R,14S). Having access to all possible candidate isomers of both petrocortyne A and its Mosher derivatives provided a secure structure assignment not so much because one of the isomers matched the natural product, but because all of the other isomers did not.

Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates

The total synthesis of two mono-THF acetogenins, tonkinecin (1) and annonacin (2), is reported in full detail. Terminal acetylene 3 prepared from D-glucono-δ-lactone and asymmetric dihydroxylation was employed as a common intermediate for both targets 1 and 2. Pd(0)-catalyzed coupling reaction of 3 with vinyl iodides 4 and 5, the chiral centers of which were taken from D-xylose and S-(-)-ethyl lactate, afforded enyne 26 and 27, respectively. Selective hydrogenation of 26 or 27 with diimide followed by removal of MOM ethers completed the synthesis of 1. A coupling reaction between the lithium derivative of 3 and epoxide 6 in the presence of boron trifluoride etherate gave 42. Both chiral centers in epoxide 6 were taken from L-ascorbic acid. Subsequent catalytic hydrogenation and MOM protection led to 43b. Introduction of the butenolide moiety by aldol condensation of protected S-lactal followed by cleavage of all MOM ethers completed the synthesis of 2.

An efficient method for the p-methoxybenzylation of hydroxy groups with 2-(4-methoxybenzyloxy)-3-nitropyridine

2-(4-Methoxybenzyloxy)-3-nitropyridine (PMBONPy), easily prepared from 2-chloro-3-nitropyridine and p-methoxybenzyl (PMB) alcohol, reacts with various types of hydroxy groups in the presence of a catalytic amount of trimethylsilyl triflate (Me3SiOTf) to give the corresponding PMB ethers in high yields under mild conditions.

Fullerodendrons: Synthesis, electrochemistry and reduction in the electrospray source for mass spectrometry analysis

The synthesis of fullerene-functionalized dendritic branches (fullerodendrons) containing C60 spheres at each branching unit has been carried out by a convergent approach using successive esterification and deprotection steps. The tert-butyl pr

Methanofullerene-functionalized dendritic branches

Fullerene-functionalized dendrons containing a C60 sphere at each branching unit have been prepared by a convergent approach using successive DCC-mediated esterifications followed by cleavage of a t-butyl ester moiety under acidic conditions.