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1) The document discusses the functionalization of α-D-glucoisosaccharino-1,4-lactone (α-ISAL) through a multi-step synthetic process to selectively modify its hydroxyl groups and enable its use as a scaffold for drug development. 2) Initial steps involved protecting the tertiary hydroxyl with Fmoc and attempts to selectively acetylate it, but the di-Fmoc lactone system proved inherently unstable. 3) Subsequent steps explored using acid conditions to cleave the Fmoc group on carbon 6, catalyzed elimination reactions to introduce a double bond, and copolymerization of the lactone ring with methyl acrylate.
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![From Polymer to Polymer:
The Journey to Functionalization of α-D-Glucoisosaccharino-1,4-lactone PIC
Background
1. Hydroxyl Protection with the
Fmoc Group
2. Reactions with
HBr : Acetic Acid System
3. Attempted Elimination Across Carbons 2
& 6
4. Copolymerisation with Methyl
Acrylate
Conclusions
Thomas Robshaw Dept. Chemical Sciences Supervisor: Professor Andrew Laws
Cellulose degrades under alkaline conditions, due to “chemical peeling”
reaction.
Large quantities of isosaccharinic acids are formed. Produced on an industrial
scale as waste product of the paper-making industry in the form of “black
liquor” (Kraft process). Different components are challenging to separate.
α-D-Glucoisosaccharinic acid (α-GISA), in 1,4-lactone form (α-ISAL), is a
good candidate for drug development molecular scaffolds (chiral centres at
carbons 2 and 4).
For full functionalization, need to demonstrate regioselective control over
reactions of the 3 hydroxyl groups.
Building on previous group work, using base-labile
9-fluorenylmethoxycarbonyl (Fmoc) group in 3-step process to selectively
acetylate tertiary hydroxyl group.
Variety of acyl transfer catalysts and reaction conditions used to improve
yield of 1st step, but limited success (see table below).
Results suggest an inherent instability in the di-Fmoc lactone system.
[A] Simple and convenient synthetic route to alkene precursor.
[B] Fmoc group on carbon 6 surprisingly cleaved under acidic
conditions, causing acyl migration and cyclisation [2].
Zn(0)-catalysed elimination, probably via Frankland oxidative
addition process.
Extremely hard to attain good yield, as over longer reaction time, Zn
acts as an electron source and reduces the double bond in-situ [3].
Reaction of bicarbonate and bromate ions generates
OH radicals, driving the addition polymerisation.
Polymers which preserve the lactone ring are rare and
have found uses in green synthesis for production of
latexes from renewable materials [4].
A number of novel γ-lactones have been synthesized
from the ISAL starting material.
Yield of key synthetic step has been improved, but not
yet to industrially viable levels.
Polymerisation represents a hitherto unreported route to
functionalization.
Project forms small part of an overall group goal to derive
value from a current industrial waste product.
Paper mills can produce
~20,000 T isosaccharinic and
xylosaccharinic acids per year [1].
[1] R. Alén, Biorefining of Forest Resources, Paper Engineers Association, Helsinki, Finland, 2011. [2] M.I. Tamboli, M.S. Shashidhar, R.G. Gonnade and S. Krishnaswamy, Chem. Eur. J., 2015, 21, 13676-13682.
[3] K. Bock, I.M. Castilla, I. Lundt and C. Pedersen, Acta Chem. Scand., 1987, 41, 13-17. [4] M. Moreno, M. Goikoetxea, J.C. de la Cal and M.J. Barandiaran, J. Polym. Sci., 2014, 52, 3543-3549.
4:1 monomeric molar ratio
OFmoc
H](https://image.slidesharecdn.com/7f5adfaf-8ce3-4bef-91ca-11803070ca47-160622191541/85/ISAL_poster-1-320.jpg)
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Katsuki Sharpless Asymmetric Epoxidation and its Synthetic Applications
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heck reaction, suzuki coupling and sharpless epoxidation
heck reaction, suzuki coupling and sharpless epoxidation
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“Alkaline Chlorine Dioxide Bleaching Of Cloned Eucalyptus Hybrid Wood 2013 an...
The bleaching chemistry indicates that pH affects the effectiveness of chlorine dioxide treatment and
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This document summarizes a study that assessed the chemical, physical, and biological properties of new and field-conditioned cross-linked polyacrylamide gels. Both new gels and gels aged 1-6 years in fields contained low levels of acrylamide and acrylic acid monomers, except when subjected to elevated temperatures which caused higher monomer release. Gel water holding capacity decreased sharply within 18 months of field placement due to environmental conditions like UV exposure and freeze/thaw cycles. Microscopy revealed that gels became increasingly colonized by fungi and bacteria over time in fields. The study concluded that cross-linked polyacrylamide placed in soil is relatively stable but loses effectiveness due to declining water retention, raising questions
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Operational parameters affecting the removal and recycling of direct blue ind...
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A comparison of cardanol and its derivatives as reactive
A comparison of cardanol and its derivatives as reactive
A comparison of cardanol and its derivatives as reactive
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ISAL_poster
- 1. From Polymer to Polymer: The Journey to Functionalization of α-D-Glucoisosaccharino-1,4-lactone PIC Background 1. Hydroxyl Protection with the Fmoc Group 2. Reactions with HBr : Acetic Acid System 3. Attempted Elimination Across Carbons 2 & 6 4. Copolymerisation with Methyl Acrylate Conclusions Thomas Robshaw Dept. Chemical Sciences Supervisor: Professor Andrew Laws Cellulose degrades under alkaline conditions, due to “chemical peeling” reaction. Large quantities of isosaccharinic acids are formed. Produced on an industrial scale as waste product of the paper-making industry in the form of “black liquor” (Kraft process). Different components are challenging to separate. α-D-Glucoisosaccharinic acid (α-GISA), in 1,4-lactone form (α-ISAL), is a good candidate for drug development molecular scaffolds (chiral centres at carbons 2 and 4). For full functionalization, need to demonstrate regioselective control over reactions of the 3 hydroxyl groups. Building on previous group work, using base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group in 3-step process to selectively acetylate tertiary hydroxyl group. Variety of acyl transfer catalysts and reaction conditions used to improve yield of 1st step, but limited success (see table below). Results suggest an inherent instability in the di-Fmoc lactone system. [A] Simple and convenient synthetic route to alkene precursor. [B] Fmoc group on carbon 6 surprisingly cleaved under acidic conditions, causing acyl migration and cyclisation [2]. Zn(0)-catalysed elimination, probably via Frankland oxidative addition process. Extremely hard to attain good yield, as over longer reaction time, Zn acts as an electron source and reduces the double bond in-situ [3]. Reaction of bicarbonate and bromate ions generates OH radicals, driving the addition polymerisation. Polymers which preserve the lactone ring are rare and have found uses in green synthesis for production of latexes from renewable materials [4]. A number of novel γ-lactones have been synthesized from the ISAL starting material. Yield of key synthetic step has been improved, but not yet to industrially viable levels. Polymerisation represents a hitherto unreported route to functionalization. Project forms small part of an overall group goal to derive value from a current industrial waste product. Paper mills can produce ~20,000 T isosaccharinic and xylosaccharinic acids per year [1]. [1] R. Alén, Biorefining of Forest Resources, Paper Engineers Association, Helsinki, Finland, 2011. [2] M.I. Tamboli, M.S. Shashidhar, R.G. Gonnade and S. Krishnaswamy, Chem. Eur. J., 2015, 21, 13676-13682. [3] K. Bock, I.M. Castilla, I. Lundt and C. Pedersen, Acta Chem. Scand., 1987, 41, 13-17. [4] M. Moreno, M. Goikoetxea, J.C. de la Cal and M.J. Barandiaran, J. Polym. Sci., 2014, 52, 3543-3549. 4:1 monomeric molar ratio OFmoc H