Cleavage of 1,3-dioxolanes by acetic anhydride to give allylic alcohol acetate derivatives

1988 ◽  
Vol 24 (1) ◽  
pp. 110-110
Author(s):  
A. A. Gevorkyan ◽  
P. I. Kazaryan ◽  
S. V. Avakyan
Keyword(s):  
Acetic Anhydride ◽  
Allylic Alcohol ◽  
Alcohol Acetate

Polybenzoate und -acetate des Phorbols und Phorbol-3-ols und funktionelle Derivate der Allylgruppierung des Phorbols

1968 ◽  
Vol 23 (11) ◽  
pp. 1430-1443 ◽  
Author(s):  
Hans Ulrich Schairer ◽  
Heinz Walter Thielmann ◽  
Michael Gschwendt ◽  
Gert Kreibich ◽  
Rainer Schmidt ◽  
...  
Keyword(s):  
Acetic Anhydride ◽  
Sodium Borohydride ◽  
Phorbol Esters ◽  
Allylic Alcohol ◽  
Hydroxyl Groups ◽  
Alcohol Group ◽  
Toluene Sulfonic Acid ◽  
Sodium Borohydride Reduction ◽  
Acetyl Migration ◽  
Tertiary Hydroxyl

Base catalysed transesterification of phorbol-12,13,20-tribenzoate yields phorbol-12,13-dibenzoate. By base catalysed transesterification of phorbol-pentaacetate phorbol-9,12,13-triacetate is obtained. This can be re-acetylated to give phorbol-9,12,13,20-tetraacetate which is also obtained by treatment of phorbol-12,13,20-triacetate with acetic anhydride/p-toluene-sulfonic acid.Reduction of phorbol-12,13,20-triacetate with LiAlH4 yields phorbol-3-ol which reduces Fehling's and Tollen's reagent. Reduction of the 3-keto group alone can be accomplished with sodium borohydride. From all phorbol-esters investigated only in phorbol-pentaacetate an acetyl migration is observed during the sodium borohydride reduction leading to phorbol-3-ol-3,9,12,13,20-pentaacetate. By these findings those two tertiary hydroxyl groups of phorbol which are not acetylated with acetic anhydride/pyridine at room temperature were further characterized.Oxidation of phorbol-12,13-diacetate with activated manganese dioxide yields phorbol-20-al-12,13-diacetate. By evaluation of nmr-spectra of this aldehyde and of some of its derivatives as well as of the epoxide of phorbol-12,13-diacetate and of 6-oxo-7-hydroxy- and 6,7-diacetoxy-20-nor-phorbol-12,13-diacetate the sequence of C-atoms around the allylic alcohol group of phorbol is further characterized.

DETERMINATION OF ALDOSTERONE AND DEOXYCORTICOSTERONE IN PLASMA USING 3H-ACETIC ANHYDRIDE AND VAPOUR PHASE ACETYLATION

1969 ◽  
Vol 61 (1_Suppl) ◽  
pp. S12 ◽  
Author(s):  
V. H. T. James ◽  
A. E. Rippon ◽  
M. L. Arnold
Keyword(s):  
Acetic Anhydride ◽  
Vapour Phase

Synthesis of the C19–C30 Bis-THF Fragment of Iriomoteolide-13a via Stepwise SN2 Cyclization and Intramolecular syn-Oxypalladation

2020 ◽  
Author(s):  
Hui Zhao ◽  
Kai Gao ◽  
Haichen Ma ◽  
Tsz Chun Yip ◽  
Wei-Min Dai
Keyword(s):  
Aldol Reaction ◽  
Allylic Alcohol ◽  
Asymmetric Dihydroxylation ◽  
Hydroxy Groups

The C19–C30 bis-THF fragment of the proposed structure of iriomoteolide-13a has been synthesized. The w-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by <i>anti</i>-aldol reaction and asymmetric dihydroxylation (AD). Upon heating in pyridine the stereotetrad underwent an S<sub>N</sub>2 cyclization to form the C19–C22 THF ring. It was followed by an intramolecular <i>syn</i>-oxypalladation of the C28 chiral allylic alcohol to give the C23–C26 THF ring.

Syntheses and Cytotoxicity Screening of some Novel 1,2,4-Triazine Derivatives against Liver Carcinoma Cell Lines

2020 ◽  
Vol 17 ◽  
Author(s):  
W. Abd El-Fattah
Keyword(s):  
Acetic Anhydride ◽  
Cell Lines ◽  
Carcinoma Cell ◽  
Aromatic Aldehydes ◽  
Liver Carcinoma ◽  
Anticancer Activities ◽  
Carcinoma Cell Lines ◽  
Elemental Analyses ◽  
Triazine Derivatives ◽  
C Nmr

: In this work, 1,2,4-triazine derivatives were synthesized and evaluated for anticancer activities. Series of 1,2,4-triazine derivatives (4a, b) were prepared via the reaction of N-benzoyl glycine (1) with aromatic aldehydes in presence of fused sodium acetate and acetic anhydride to give 1,3-oxazolinone derivatives (2a, b), followed by condensation with 1-(ethoxycarbonyl) hydrazine (3) in glacial acetic acid. Compounds (4a, b) then reacted with acetic anhydride, ethyl chloroacetate and 2,4-dinitrophenyl hydrazine yielded the corresponding to N-acetyl derivatives (5a, b), N-(ethoxycarbonyl) methyl derivative (6) and 1,2-disubstituted hydrazine (7), respectively. The structures of the 1,2,4-triazine derivatives were confirmed by IR, 1H, 13C NMR, MS and elemental analyses. Anticancer activity of some 1,2,4-triazine derivatives (4-7) have been investigated. The results revealed that compounds 4a (IC50= 2.7μM), 5a (IC50= 1.5μM), and 5b (IC50= 3.9μM) show promising inhibitory growth efficacy compared to a standard antitumor drug (IC50= 4.6μM). These three compounds can be considered as potential agents against human hepatocellular carcinoma cell lines (HepG-2).

Synthesis of conjugates of 1-(carboxymethyl)cytosine and 1-(5-O-carboxymethyl-β-D-arabinofuranosyl)cytosine with proteins

1979 ◽  
Vol 44 (10) ◽  
pp. 3023-3032 ◽  
Author(s):  
Helmut Pischel ◽  
Antonín Holý ◽  
Günther Wagner
Keyword(s):  
Human Serum Albumin ◽  
Acetic Anhydride ◽  
Serum Albumin ◽  
Human Serum ◽  
Activated Esters ◽  
Hydrolysis Of

1-(Carboxymethyl)cytosine (Ia), 1-(5-O-carboxymethyl-β-D-arabinofuranosyl)cytosine (IIa) and 5'-O-carboxylmethylcytidine (IIIa) were transformed by treatment with acetic anhydride and 4-dimethylaminopyridine to the peracetyl derivatives Ib-IIIb. These products reacted with p-nitrophenol in the presence of N, N'-dicyclohexylcarbodiimide to give the activated esters Ic-IIIc which on reaction with ammonia, dimethylamine or 2-aminoethanol afforded the corresponding carboxamides Id-IIId, IIe,f. Reactions of Ic and IIc with human serum albumin and bovine γ-globulin at pH 9.2, followed by hydrolysis of the N- or O-acetyl groups at pH 9.5, gave 50% up to 64% yields of the respective conjugates Ig, IIg and Ih, IIh.

An unusual reaction of a bridged triterpenoid α-diketone with acetic anhydride

1991 ◽  
Vol 56 (12) ◽  
pp. 2917-2935 ◽  
Author(s):  
Eva Klinotová ◽  
Václav Křeček ◽  
Jiří Klinot ◽  
Miloš Buděšínský ◽  
Jaroslav Podlaha ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Acetic Anhydride ◽  
Spectral Methods ◽  
X Ray Diffraction ◽  
X Ray ◽  
Mild Conditions ◽  
Condensation Products ◽  
Unsaturated Lactones ◽  
C Nmr

3β-Acetoxy-21,22-dioxo-18α,19βH-ursan-28,20β-olide (IIIa) reacts with acetic anhydride in pyridine under very mild conditions affording β-lactone IVa and γ-lactones Va and VIIa as condensation products. On reaction with pyridine, lactones Va and VIIa undergo elimination of acetic acid to give unsaturated lactones VIIIa and IXa, respectively. Similarly, the condensation of 20β,28-epoxy-21,22-dioxo-18α,19βH-ursan-3β-yl acetate (IIIb) with acetic anhydride leads to β-lactone IVb and γ-lactone Vb; the latter on heating with pyridine affords unsaturated lactone VIIIb and 21-methylene-22-ketone Xb. The structure of the obtained compounds was derived using spectral methods, particularly 1H and 13C NMR spectroscopy; structure of lactone IVa was confirmed by X-ray diffraction.

Microporous Membranes from an Insoluble Polyimide

1995 ◽  
Vol 60 (10) ◽  
pp. 1741-1746
Author(s):  
Jan Schauer ◽  
Miroslav Marek
Keyword(s):  
Acetic Anhydride ◽  
Phase Inversion ◽  
Amic Acid ◽  
Microporous Membranes ◽  
Inversion Process ◽  
Phase Inversion Process ◽  
Ultrafiltration Process

Poly(amic acid) prepared from 3,3',4,4'-benzophenonetetracarboxylic dianhydride and bis(4-aminophenyl) ether was used for preparation of microporous membranes by the phase inversion process. Membranes coagulated in acetic anhydride were brittle but usable for ultrafiltration. Coagulation of the poly(amic acid) in water or lower alcohols and subsequent thermal cyclocondensation led to extremely brittle polyimides, which limits their use for ultrafiltration process.

scholarly journals Synthesis of a sucrose dimer with enone tether; a study on its functionalization

2014 ◽  
Vol 10 ◽  
pp. 1246-1254 ◽  
Author(s):  
Zbigniew Pakulski ◽  
Norbert Gajda ◽  
Magdalena Jawiczuk ◽  
Jadwiga Frelek ◽  
Piotr Cmoch ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Double Bond ◽  
Carbonyl Group ◽  
Osmium Tetroxide ◽  
Cd Spectroscopy ◽  
Allylic Alcohol ◽  
Circular Dichroïsm

The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was oxidized with osmium tetroxide to a diol. Absolute configurations of the allylic alcohol as well as the diol were determined by circular dichroism (CD) spectroscopy using the in situ dimolybdenum methodology.

Decay resistance of acetic anhydride modified wood: a review

2013 ◽  
Vol 4 (3) ◽  
pp. 137-143 ◽  
Author(s):  
G Alfredsen ◽  
P O Flæte ◽  
H Militz
Keyword(s):  
Acetic Anhydride ◽  
Decay Resistance ◽  
Modified Wood
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