Applicability of Methyl 2,3,4-Tri-O-benzoyl-1-methanesulfonyl-a-D-glucopyranuronate as a Novel Quaternary Glucuronyl Reagent for Tertiary Amines

Araya, Ichiro; Akita, Hiroyuki

doi:10.3987/com-07-11289

Cited by 5 publications

(2 citation statements)

References 2 publications

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“…The anomeric O-methanesulfonate 153 has also been used to alkylate amines; a range of pyridine, imidazole and bicyclic heterocyclic amines gave yields from 32-88%, but aliphatic amines did not react. 176 There is clearly a problem with more basic amines: it is notable that nicotine 154 and related mixed heteroaromatic/aliphatic amines always alkylate on the pyridine nitrogen.…”

Section: N-glucuronidesmentioning

confidence: 99%

Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Stachulski

Meng

2013

Nat. Prod. Rep.

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Covering: 1998 to 2011. Previous review: Nat. Prod. Rep., 1998, 15, 173-186. The fourteen years that have passed since the previous review on this topic have seen a significant increase of interest in many aspects of glucuronide chemistry and biology. Glucuronides are the most important class of phase 2 xenobiotic metabolites and typically act in a detoxifying role. While this is generally true for O-alkyl and O-aryl glucuronides, a number of glucuronides are known to be pharmacologically active per se. Additionally the use of glucuronide prodrugs, notably to ameliorate the cytotoxicity of anticancer agents, has markedly increased. Whereas the previous review covered only the synthesis of O-glucuronides, we now include N-, S- and C-glucuronides also and discuss both synthetic and biological aspects. Synthetic methods for all classes of glucuronides are reviewed and updated, together with advances in the enzymatic synthesis of glucuronides and methods for their detection. Finally we discuss the biological reactivity of glucuronides where known, including the important morphine-6-glucuronide. A lively debate has continued for several years on whether O-acyl glucuronide metabolites of carboxylic acids are toxic, affecting both the safety assessment of well-used drugs and new drug development programmes. We summarise the current understanding, together with other known examples of interaction between glucuronides and macromolecules.

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Section: N-glucuronidesmentioning

confidence: 99%

Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Stachulski

Meng

2013

Nat. Prod. Rep.

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“…Invariably elimination predominates with such strong bases, leading to the glycal 7 as the major product: 15 we have obtained similar results in the glucose series. While this work was being written a new report appeared, 16 describing quaternisation via an anomeric mesylate, but this was still ineffective for aliphatic tertiary amines.…”

Section: Introductionmentioning

confidence: 96%

Syntheses and structures of anomeric quaternary ammonium β-glucosides and comments on the anomeric C–N bond lengths

et al. 2009

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Preparation of THP‐Ester‐Derived Pyridinium‐Type Salts and their Reactions with Various Nucleophiles

Fujioka

Minamitsuji

Moriya

et al. 2012

Chemistry An Asian Journal

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Nucleophilic substitution at the anomeric positions of tetrahydropyranyl (THP) and related carbohydrate-derived esters that proceeded through pyridinium-type salt intermediates have been developed. Treatment of the 6-substituted α-acetoxy-tetrahydropyrans with TMSOTf (TMS=trimethylsilyl) and 2-substitutited pyridines, such as 2-p-tolylpyridine and 2-methoxypyridine, led to the efficient generation of cis-pyridinium-type salts. These salts reacted with various nucleophiles, such as alcohols, azides, and organozinc reagents, to form nucleophilic-substitution products. A characteristic feature of these processes was that they took place under mild conditions, which did not affect acid-labile protecting groups. Furthermore, the reactions that employed azides and C-nucleophiles generated 2,6-trans products with high degrees of stereoselectivity.

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Applicability of Methyl 2,3,4-Tri-O-benzoyl-1-methanesulfonyl-a-D-glucopyranuronate as a Novel Quaternary Glucuronyl Reagent for Tertiary Amines

Cited by 5 publications

References 2 publications

Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Syntheses and structures of anomeric quaternary ammonium β-glucosides and comments on the anomeric C–N bond lengths

Preparation of THP‐Ester‐Derived Pyridinium‐Type Salts and their Reactions with Various Nucleophiles

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