Flavonoid intermediates for the synthesis of mopanol trimethyl ether[trans-trans-7,7',8'-Trimethoxyisochromano(4',3':2,3)chroman-4-ol]

1976 ◽  
Vol 29 (1) ◽  
pp. 191 ◽  
Author(s):  
JW Clark-Lewis ◽  
DP Cox
Keyword(s):  
Carboxylic Acid ◽  
Potassium Carbonate ◽  
Dimethyl Sulphate ◽  
Metal Hydrides ◽  
Cyclic Ether ◽  
Protecting Group ◽  
Model Compounds ◽  
Initial Product ◽  
Dibenzyl Ether ◽  
Trimethyl Ether

Preparation of a number of intermediates for the synthesis of (�)-mopanol trimethyl ether is described, together with exploratory reactions with model compounds, and especially with 7-methoxyflavanone-2'-carboxylic acid. 7-Methoxyflavan-4-ol, the initial product from reduction of 7-methoxyflavanone-2'-carboxylic acid with complex metal hydrides, was found to undergo facile dehydration to a novel intramolecular dibenzyl ether [the cyclic ether (19)*]. It was noted that the methoxymethyl group, which may be used as a protecting group for phenols, did not survive the conditions of methylation with dimethyl sulphate and potassium carbonate in acetone.

scholarly journals Thioether-Catalysed Tandem Synthesis of Furans and Cyclic Ethers or Lactones

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1358-1362 ◽  
Author(s):  
J. Clark ◽  
Verena Klaus
Keyword(s):  
Carboxylic Acid ◽  
Cyclic Ether ◽  
Single Step ◽  
Cyclic Ethers ◽  
The Creation ◽  
Tandem Synthesis

Acyclic conjugated ynenediones tethered to an alcohol or carboxylic acid are converted into furanyl-substituted cyclic ethers or lactones in a single step by treatment with the tetrahydrothiophene. Modest levels of diastereocontrol can be achieved in some cases where the presence of a substituent on the tether results in the creation of a second stereogenic centre upon formation of the cyclic ether or lactone.

13C Nuclear Magnetic Resonance Studies. 29. 13C Spectra of Some Alicyclic Methyl Esters

1973 ◽  
Vol 51 (13) ◽  
pp. 2092-2097 ◽  
Author(s):  
M. Gordon ◽  
S. H. Grover ◽  
J. B. Stothers
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Carboxylic Acid ◽  
Magnetic Resonance ◽  
Methyl Esters ◽  
Membered Ring ◽  
Model Compounds ◽  
Magnetic Resonance Studies ◽  
13C Nuclear Magnetic Resonance ◽  
Acid Esters ◽  
Shielding Effects

The shielding effects of the carbomethoxyl group on neighboring carbons in the cyclohexane and trans-decalin ring systems have been characterized by 13C n.m.r. examination often model compounds. The data show that sufficient differences are exhibited by axial and equatorial groups to permit stereochemical assignments in related systems. The observed trends are compared with those produced by other functional groups. The three-, four-, and five-membered ring cycloalkae carboxylic acid esters were also examined.

Semipermanent C-Terminal Carboxylic Acid Protecting Group: Application to Solubilizing Peptides and Fragment Condensation

2014 ◽  
Vol 17 (2) ◽  
pp. 294-297 ◽  
Author(s):  
Marta Paradís-Bas ◽  
Judit Tulla-Puche ◽  
Fernando Albericio
Keyword(s):  
Carboxylic Acid ◽  
Protecting Group ◽  
Fragment Condensation

One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate

2006 ◽  
Vol 47 (22) ◽  
pp. 3629-3631 ◽  
Author(s):  
Kande K.D. Amarasinghe ◽  
Matthew B. Maier ◽  
Anil Srivastava ◽  
Jeffrey L. Gray
Keyword(s):  
Carboxylic Acid ◽  
Potassium Carbonate ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Esters

Studies of dialkyl ether phospholipids. I. Chemical synthesis of some model compounds

1970 ◽  
Vol 48 (5) ◽  
pp. 585-593 ◽  
Author(s):  
Jung-Shou Chen ◽  
Peter G. Barton
Keyword(s):  
Chemical Synthesis ◽  
Free Product ◽  
Methyl Iodide ◽  
Cadmium Chloride ◽  
Chloride Complex ◽  
Protecting Group ◽  
Subsequent Reaction ◽  
Model Compounds ◽  
Ether Phospholipids ◽  
Catalytic Hydrogenolysis

The syntheses of three 1,2-dialkyl-sn-glycero-3-phosphates and one new 1,2-dialkyl-sn-glycerol are described. 1,2-Dioctadecyl-sn-glycero-3-phosphate was obtained by phosphorylation of 1,2-dioctadecyl-sn-glycerol with diphenylphosphorodichloridate and subsequent catalytic hydrogenolysis. 1,2-Dioctadecyl-sn-glycero-3-(methyl)phosphorylcholine was prepared by phosphorylation of the same dialkyl glycerol with methylphosphorodichloridate and subsequent reaction with choline iodide. 1,2-Dimethyl-sn-glycerol was prepared by treatment of 3-benzyl-sn-glycerol with methyl iodide and KOH followed by hydrogenolysis to remove the protecting group. This compound was then phosphorylated with phenylphosphorodichloridate, the product allowed to react with choline iodide, and the iodide-free product hydrogenated catalytically to yield 1,2-dimethyl-sn-glycero-3-phosphorylcholine which was characterized as the cadmium chloride complex. Some improvements in an established synthesis of 1,2-dioctadecyl-sn-glycerol are described.

Synthesis of robustol trimethyl ether

1973 ◽  
Vol 26 (10) ◽  
pp. 2277 ◽  
Author(s):  
JR Cannon ◽  
BW Metcalf
Keyword(s):  
Model Compounds ◽  
New Synthesis ◽  
Trimethyl Ether

The macrocyclic substance robustol trimethyl ether (2) has been synthesized by an unambiguous method. ��� During a study of the reactions of model compounds a new synthesis of 1,14-bis-(3?,5?-dimethoxyphenyl)tetradecane (4) has been developed.

scholarly journals Exploring hydrogen peroxide responsive thiazolidinone-based prodrugs

2015 ◽  
Vol 51 (33) ◽  
pp. 7116-7119 ◽  
Author(s):  
Christian Perez ◽  
Jean-Philippe Monserrat ◽  
Yao Chen ◽  
Seth M. Cohen
Keyword(s):  
Hydrogen Peroxide ◽  
Carboxylic Acid ◽  
Protecting Group

A thiazolidinone moiety was found to serve as a protecting group for releasing carboxylic acid-containing therapeutics in the presence of hydrogen peroxide.

One-Pot Synthesis of 1,2,4-Oxadiazoles from Carboxylic Acid Esters and Amidoximes Using Potassium Carbonate.

ChemInform ◽  
2006 ◽  
Vol 37 (36) ◽  
Author(s):  
Kande K. D. Amarasinghe ◽  
Matthew B. Maier ◽  
Anil Srivastava ◽  
Jeffrey L. Gray
Keyword(s):  
Carboxylic Acid ◽  
Potassium Carbonate ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Esters
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