Advances in Chemical Synthesis of Fondaparinux

Ding, Yili; Prasad, Chamakura V.N.S. Vara; Wang, Bingyun

doi:10.1155/2019/9545297

Cited by 6 publications

(3 citation statements)

References 29 publications

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“…As an extension of random glycosylation, Ding et al reported the double random glycosylation starting with an unprotected monosaccharide for the synthesis of a trisaccharide library. The target library and its synthesis through a double random glycosylation strategy is summarized in Scheme .…”

Section: Discussionmentioning

confidence: 99%

Glycosylation on Unprotected or Partially Protected Acceptors

Ding

Prasad²,

Wang

2020

Eur J Org Chem

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Over the last 30 years, there have been several methods developed for the synthesis of oligosaccharides, such as combinatorial synthesis, programmable one‐pot glycosylations, pre‐activation‐based chemo‐selective glycosylation strategy, random glycosylation, chemo‐enzymatic processes, and automated platforms. Distinguishing hydroxyl groups in carbohydrate monomers form the crux of oligosaccharides synthesis. The protection of hydroxyl groups stops glycosylation at undesired positions on carbohydrates, but additional steps are required to install and remove the protecting groups. The targeted functionalization of carbohydrates relies mostly on the protection of hydroxyl groups that are not supposed to undergo glycosylation and to leave the hydroxyl group unprotected where the glycosylation should occur. Numerous procedures to avoid or decrease protecting group manipulations have been developed for the synthesis of a single or an oligosaccharide library, such as glycosylation on unprotected or partially protected acceptors, and random glycosylation on unprotected acceptors. In this review, overall approaches for glycosylation on unprotected or partially protected acceptors in the synthesis of oligosaccharides and oligosaccharide libraries are summarized, the glycosylation on unprotected or partially protected carbohydrate acceptors with or without tin or boron mediation, and random glycosylation on unprotected or partially protected acceptors in solution phase or on solid phase are discussed.

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Section: Discussionmentioning

confidence: 99%

Glycosylation on Unprotected or Partially Protected Acceptors

Ding

Prasad²,

Wang

2020

Eur J Org Chem

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“…The assembly of this complex molecule on a commercial scale has asked for the development of sophisticated chemistry, which has been recently reviewed. 61,62 Different strategies have been developed for the assembly of Fondaparinux, using glucuronic and iduronic acid monosaccharides 63,64 or using a late-stage oxidation approach. 65,66 Nadji et al reported the synthesis of Fondaparinux (depicted in Scheme 4), that delivered the product on an industrial scale of 516 g in an overall 0.0338% yield over 28 steps, 67 which is one of the efficient methods for industrial grade synthesis.…”

Section: Heparin (Hp) and Heparan Sulfate (Hs)mentioning

confidence: 99%

Synthesis of Uronic Acid Containing Oligosaccharides

Wang

Marel

et al. 2021

Comprehensive Glycoscience

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“…3 Fondaparinux has 100% absolute bioavailability subcutaneously (SC), instant onset of action, a long half-life (terminal half-life of 17-21 hours), direct renal excretion, and fewer adverse reactions when compared with direct oral anticoagulants. [4][5][6] The efficacy and safety of fondaparinux in the prevention of VTE in lower extremities during major orthopedic surgeries and in high-risk abdominal surgery has been demonstrated in many clinical studies and it has been found to be superior or non-inferior to other antithrombotic agents. [7][8][9][10][11][12][13] For the past 2 decades, fondaparinux has been one of the mainstays for VTE prevention in acutely ill adult patients.…”

Section: Introductionmentioning

confidence: 99%

Fondaparinux Sodium: Recent Advances in the Management of Thrombosis

Bauersachs

2023

J Cardiovasc Pharmacol Ther

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Fondaparinux sodium is a chemically synthesized selective factor Xa inhibitor approved for the prevention and treatment of venous thromboembolic events, that is, deep vein thrombosis, pulmonary embolism, and superficial vein thrombosis, in acutely ill (including those affected by COVID-19 or cancer patients) and those undergoing surgeries. Since its approval in 2002, the efficacy and safety of fondaparinux is well demonstrated by many clinical studies, establishing the value of fondaparinux in clinical practice. Some of the advantages with fondaparinux are its chemical nature of synthesis, minimal risk of contamination, 100% absolute bioavailability subcutaneously, instant onset of action, a long half-life, direct renal excretion, fewer adverse reactions when compared with direct oral anticoagulants, and being an ideal alternative in conditions where oral anticoagulants are not approved for use or in patients intolerant to low molecular weight heparins (LMWH). In the last decade, the real-world use of fondaparinux has been explored in other conditions such as acute coronary syndromes, bariatric surgery, in patients developing vaccine-induced immune thrombotic thrombocytopenia (VITT) and in pregnant women with heparin-induced thrombocytopenia (HIT), or those intolerant to LMWH. The emerging data from these studies have culminated in recent updates in the guidelines that recommend the use of fondaparinux under various conditions. This paper aims to review the recent data and the subsequent updates in the recommendations of various guidelines on the use of fondaparinux sodium.

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Advances in Chemical Synthesis of Fondaparinux

Cited by 6 publications

References 29 publications

Glycosylation on Unprotected or Partially Protected Acceptors

Glycosylation on Unprotected or Partially Protected Acceptors

Synthesis of Uronic Acid Containing Oligosaccharides

Fondaparinux Sodium: Recent Advances in the Management of Thrombosis

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