32938-33-3

Usage

InChI:InChI=1/C16H16O4/c1-18-11-8-9-15(20-3)13(10-11)16(17)12-6-4-5-7-14(12)19-2/h4-10H,1-3H3

Upstream product

• 21615-34-9 2-Methoxybenzoyl chloride 
• 150-78-7 1,4-dimethoxybezene 
• 579-75-9 2-Methoxybenzoic acid 

Downstream Products

• 1915-98-6 2-hydroxy-9H-xanthen-9-one 
• 42833-51-2 (2-Hydroxy-5-methoxy-phenyl)-(2-methoxy-phenyl)-methanone 
• 83570-57-4 2,2'-dihydroxy-5-methoxy benzophenone 
• 134268-11-4 2-(2,5-dimethylphenyl)-2-(2-methylphenyl)-1-methylethyl ethyl ether 
• 134285-83-9 2,5-dimethylphenyl(2-methylphenyl)methyl methyl ether 
• 134267-95-1 2,5-dimethoxyphenyl(2'-methoxxyphenyl)diazomethane 
• 134268-09-0 5-methoxy-3-(2-methoxyphenyl)dihydrobenzofuran 
• 134268-10-3 3-(2,5-dimethoxyphenyl)dihydrobenzofuran 
• 134268-31-8 2,2',5'-trimethoxybenzophenone hydrazone 

Relevant academic research and scientific papers

Preparation and applications of xanthenylamide (XAL) handles for solid-phase synthesis of C-terminal peptide amides under particularly mild conditions

[[9-[(9-Fluorenylmethyloxycarbonyl)amino]xanthen-2(or 3)-yl]oxy]alkanoic acid (XAL) handles have been prepared by efficient four-step routes from 2- or 3-hydroxyxanthone and coupled onto a range of amino-functionalized supports. The resultant XAL supports are the starting points for solid-phase peptide synthesis by Fmoc chemistry. Upon completion of chain assembly, C-terminal peptide amides are released in excellent yields and purities by use of low concentrations [1-5% (v/v)] of trifluoroacetic acid (TFA) in dichloromethane, often without a need for added carbocation scavengers. These cleavage conditions allow retention of all or a significant portion of tert-butyl type and related side-chain protecting groups, which subsequently may be removed fully in a solution process carried out at higher acid concentration. XAL supports are particularly useful for the synthesis of acid-sensitive peptides, including tryptophan-containing sequences that are known to be susceptible to yield- and/or purity-reducing alkylation side reactions. The effectiveness of this chemistry was shown with the syntheses of prothrombin (1-9), acyl carrier protein (65-74), Tabanus atratus adipokinetic hormone, fragments of the protein RHK 1, CCK-8 sulfate, and oxytocin. Furthermore, the application of XAL supports for the preparation of fully protected peptide amides has been demonstrated.

BeCl2 as a new highly selective reagent for dealkylation of aryl-methyl ethers

An efficient and simple method is introduced for the selective removal of methyl group from poly aryl-methyl ethers, in some important derivatives of benzophenones, xanthones, anthraquinones, aryl esters, benzamides and nitroanisoles with BeCl2.

Xanthenylamide handle for use in peptide synthesis

The preparation and properties of xanthenylamide handles for use in peptide synthesis is disclosed. The compounds, Fmoc-9H-2-alkyleneoxycarboxy-xanthene-9-amines, are used as peptide handles in the solid phase synthesis of peptide amides.

Buttressing Effect in Carbene Chemistry. Effect of 3-Alkyl Groups on the Reactions of 2-Alkoxydiphenylcarbenes

Irradiation of 2-methoxydiphenyldiazomethane 1a in diethyl ether at 10 deg C gave 3-phenyldihydrobenzofuran 3a along with a small amount of the ether adduct 4a, which became the major product when the irradiation was carried out in the ether matrix at -196 deg C.The reaction patterns were dramatically changed as an alkyl group was introduced into the 3-position of substrates 1.Thus, irradiation of 2-methoxy-3-alkyldiphenyldiazomethanes 1b-d in diethyl ether either at 10 deg C or at -196 deg C afforded the corresponding benzofurans 3b-d at the complete expense of the ether adducts 4b-d.The results are nicely explained in terms of the buttressing effect of the 3-alkyl group, which prevents the 2-methoxy group from lying in the plane of the phenyl ring in the precursor molecules and assists the methoxy group in rotating around the C-O bond toward the carbene centre after elimination of N2.Generation of carbenes 2 in methanol at 10 deg C produced O-H insertion adducts 5 as the major product at the expense of benzofurans 3.The ether 5a was formed as a major product in the reaction of carbene 2a with the alcohol matrix at -196 deg C, but the benzofurans 3 became the major product in the irradiation of substrates 1b-d in methanol matrix at -196 deg C.The results are again explicable in terms of the buttressing effect of 3-alkyl substituents on the relative populations of thew rotational isomers of the carbenes 2.The effect of the 3-alkyl group on the reaction of 2,2',5'-trimethoxydiphenylcarbenes 7 which form two kinds of intramolecular C-H insertion products 8 and 9 were studied and the results are again discussed in terms of the buttressing effect.