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New Methods for the Synthesis of O-A...

Perrie, Jennifer Anne,

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New Methods for the Synthesis of O-Alkyl and Acyl Glucuronides /

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	New Methods for the Synthesis of O-Alkyl and Acyl Glucuronides // Jennifer Anne Perrie.
作者:	Perrie, Jennifer Anne,
面頁冊數:	1 electronic resource (227 pages)
附註:	Source: Dissertations Abstracts International, Volume: 70-12, Section: B.
Contained By:	Dissertations Abstracts International70-12B.
標題:	Iodine. -
電子資源:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=U488739
ISBN:	9798377699927

New Methods for the Synthesis of O-Alkyl and Acyl Glucuronides /
Perrie, Jennifer Anne,

New Methods for the Synthesis of O-Alkyl and Acyl Glucuronides /Jennifer Anne Perrie. - 1 electronic resource (227 pages)

Source: Dissertations Abstracts International, Volume: 70-12, Section: B.

Glucuronides are an important class of metabolites. They are formed by the coupling of a carbohydrate moiety (glucuronic acid), with an aglycone. Often they are the final form of a drug when it is excreted from the body. It is therefore important to be able to synthesise these compounds for use as reference samples, for toxicological evaluation of new medicines, and as potential drugs in their own right. C-, N-, S- and O-glucuronides may all be formed. This study focuses on the chemical synthesis of O-glucuronides.Initially studies were carried out on the imidate coupling procedure (Scheme A), which is becoming increasingly popular. The factors affecting this process were investigated, namely: catalyst; protecting group on the sugar; and order of addition. Several steroidal glucuronides were synthesised in this way.The Koenigs-Knorr method for synthesising glucuronides employs a bromosugar and heavy metal catalysts. As an alternative the disarmed tri-pivaloyl iodosugar (II) was synthesised. TIT proved to be an excellent glycosyl donor (Scheme B), which could be activated most successfully using FeCl3/CuCl and iodine or NIS and iodine.Acyl glucuronides are reactive metabolites that can bind to proteins and can have toxicological implications. They rearrange readily at acidic and basic pH making their synthesis more difficult. Here a convenient synthetic route is reported in three steps from the readily available glucuronic acid (VI), Scheme C,Acyl glucuronides of steroidal compounds and well known NSAIDs have been synthesised along with a couple of di-saccharides. The yields are high and the a:B selectivity, which often causes a problem in the synthesis of this class of compounds, is excellent.

English

ISBN: 9798377699927Subjects--Topical Terms:

2147588
Iodine.

New Methods for the Synthesis of O-Alkyl and Acyl Glucuronides /
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520 $a Glucuronides are an important class of metabolites. They are formed by the coupling of a carbohydrate moiety (glucuronic acid), with an aglycone. Often they are the final form of a drug when it is excreted from the body. It is therefore important to be able to synthesise these compounds for use as reference samples, for toxicological evaluation of new medicines, and as potential drugs in their own right. C-, N-, S- and O-glucuronides may all be formed. This study focuses on the chemical synthesis of O-glucuronides.Initially studies were carried out on the imidate coupling procedure (Scheme A), which is becoming increasingly popular. The factors affecting this process were investigated, namely: catalyst; protecting group on the sugar; and order of addition. Several steroidal glucuronides were synthesised in this way.The Koenigs-Knorr method for synthesising glucuronides employs a bromosugar and heavy metal catalysts. As an alternative the disarmed tri-pivaloyl iodosugar (II) was synthesised. TIT proved to be an excellent glycosyl donor (Scheme B), which could be activated most successfully using FeCl3/CuCl and iodine or NIS and iodine.Acyl glucuronides are reactive metabolites that can bind to proteins and can have toxicological implications. They rearrange readily at acidic and basic pH making their synthesis more difficult. Here a convenient synthetic route is reported in three steps from the readily available glucuronic acid (VI), Scheme C,Acyl glucuronides of steroidal compounds and well known NSAIDs have been synthesised along with a couple of di-saccharides. The yields are high and the a:B selectivity, which often causes a problem in the synthesis of this class of compounds, is excellent.
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