ChemInform Abstract: THERMOLYSIS OF (SILYL)METHYL-BENZYL-ETHERS, EVIDENCE FOR ANCHIMERICALLY ACCELERATED BOND HOMOLYSIS

1975 ◽  
Vol 6 (24) ◽  
pp. no-no
Author(s):  
M. T. REETZ ◽  
M. KLIMENT
Keyword(s):  
Benzyl Ethers ◽  
Bond Homolysis

Visible Light-Mediated Oxidative Debenzylation

2020 ◽  
Author(s):  
Cristian Cavedon ◽  
Eric T. Sletten ◽  
Amiera Madani ◽  
Olaf Niemeyer ◽  
Peter H. Seeberger ◽  
...  
Keyword(s):  
Reaction Time ◽  
Visible Light ◽  
Functional Groups ◽  
Continuous Flow ◽  
Protecting Groups ◽  
Benzyl Ether ◽  
Complex Molecules ◽  
Protective Groups ◽  
Benzyl Ethers ◽  
Harsh Conditions

Protecting groups are key in the synthesis of complex molecules such as carbohydrates to distinguish functional groups of similar reactivity. The harsh conditions required to cleave stable benzyl ether protective groups are not compatible with many other protective and functional groups. The mild, visible light-mediated debenzylation disclosed here renders benzyl ethers orthogonal protective groups. Key to success is the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as stoichiometric or catalytic photooxidant such that benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time for this transformation can be reduced from hours to minutes in continuous flow. <br>

A Facile, Efficient and Selective Deprotection of P - Methoxy Benzyl Ethers Using Zinc (II) Trifluoromethanesulfonate

2019 ◽  
Vol 16 (12) ◽  
pp. 955-958
Author(s):  
Reddymasu Sireesha ◽  
Reddymasu Sreenivasulu ◽  
Choragudi Chandrasekhar ◽  
Mannam Subba Rao
Keyword(s):  
Room Temperature ◽  
Protecting Groups ◽  
Side Reactions ◽  
Reaction Conditions ◽  
Acid Sensitivity ◽  
Time Period ◽  
Protective Groups ◽  
Benzyl Ethers ◽  
Last Stage ◽  
Zinc Triflate

: Deprotection is significant and conducted over mild reaction conditions, in order to restrict any more side reactions with sensitive functional groups as well as racemization or epimerization of stereo center because the protective groups are often cleaved at last stage in the synthesis. P - Methoxy benzyl (PMB) ether appears unique due to its easy introduction and removal than the other benzyl ether protecting groups. A facile, efficient and highly selective cleavage of P - methoxy benzyl ethers was reported by using 20 mole% Zinc (II) Trifluoromethanesulfonate at room temperature in acetonitrile solvent over 15-120 min. time period. To study the generality of this methodology, several PMB ethers were prepared from a variety of substrates having different protecting groups and subjected to deprotection of PMB ethers using Zn(OTf)2 in acetonitrile. In this methodology, zinc triflate cleaves only PMB ethers without affecting acid sensitivity, base sensitivity and also chiral epoxide groups.

Synthesis and Anti-Cancer Activities of Aryl Benzyl Ethers with Fluoro Substituents

2014 ◽  
Vol 11 (6) ◽  
pp. 736-741 ◽  
Author(s):  
Yi Jiang ◽  
Hong Xu ◽  
Li Liu ◽  
Rui He ◽  
Xiaomei Song ◽  
...  
Keyword(s):  
Anti Cancer ◽  
Benzyl Ethers

Benzyl ethers of methyl α-D-glucopyranoside

1980 ◽  
Vol 45 (7) ◽  
pp. 1959-1963 ◽  
Author(s):  
Dušan Joniak ◽  
Božena Košíková ◽  
Ludmila Kosáková
Keyword(s):  
Kinetic Study ◽  
Spectrophotometric Determination ◽  
Reductive Cleavage ◽  
Ether Bond ◽  
Benzyl Ethers ◽  
Acid Catalyzed ◽  
Model Substances ◽  
Hydrolysis Of

Methyl 4-O-(3-methoxy-4-hydroxybenzyl) and methyl 4-O-(3,5-dimethoxy-4-hydroxybenzyl)-α-D-glucopyranoside and their 6-O-isomers were prepared as model substances for the ether lignin-saccharide bond by reductive cleavage of corresponding 4,6-O-benzylidene derivatives. Kinetic study of acid-catalyzed hydrolysis of the compounds prepared was carried out by spectrophotometric determination of the benzyl alcoholic groups set free, after their reaction with quinonemonochloroimide, and it showed the low stability of the p-hydroxybenzyl ether bond.

A versatile iodo(iii)etherification of terminal ethynylsilanes using BF3–OiPr2 and alkyl benzyl ethers

2021 ◽  
Author(s):  
Takuya Matsumoto ◽  
Hiroshi Hagiyama ◽  
Kanetsugu Kuribayashi ◽  
Kazuhito Hioki ◽  
Hikaru Fujita ◽  
...  
Keyword(s):  
Benzyl Ether ◽  
Alkoxyl Group ◽  
Group Transfer ◽  
Benzyl Ethers

BF3–OiPr2 and alkyl benzyl ether combining system enables a chemoselective alkoxyl group transfer in the synthesis of (E)-α-silyl-β-alkoxyvinyl-λ3-iodanes.

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