Catalytic removal of tert-butyldimethylsilyl (TBS) ether by PVP-I

Lu, Guangying; Wang, Di; Ren, Jiangmeng; Ke, Yanxiong; Zeng, Bu‐Bing

doi:10.1016/j.tetlet.2019.05.059

Cited by 4 publications

(1 citation statement)

References 36 publications

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“…However, this protocol is not suitable for purine derivatives due to the cleavage of the glycosidic bond in the acidic reaction medium. Other TBS deprotection methods using povidone-iodine (PVP-1) [44] or phosphomolybdic acid [45] were not successful.…”

Section: Scheme 1 Regioselective Enzymatic Acylation Ofmentioning

confidence: 99%

Sustainable Protocol for the Synthesis of 2′,3′-Dideoxynucleoside and 2′,3′-Didehydro-2′,3′-dideoxynucleoside Derivatives

Martín-Nieves

Sanghvi²,

Fernández

et al. 2022

Molecules

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An improved protocol for the transformation of ribonucleosides into 2’,3’-dideoxynucleoside and 2’,3’-didehydro-2’,3’-dideoxynucleoside derivatives, including the anti-HIV drugs stavudine (d4T), zalcitabine (ddC) and didanosine (ddI), was established. The process involves radical deoxygenation of xanthate using environmentally friendly and low-cost reagents. Bromoethane or 3-bromopropanenitrile was the alkylating agent of choice to prepare the ribonucleoside 2′,3′-bisxanthates. In the subsequent radical deoxygenation reaction, tris(trimethylsilyl)silane and 1,1’-azobis(cyclohexanecarbonitrile) were used to replace hazardous Bu3SnH and AIBN, respectively. In addition, TBAF was substituted for camphorsulfonic acid in the deprotection step of the 5′-O-silyl ether group, and an enzyme (adenosine deaminase) was used to transform 2’,3’-dideoxyadenosine into 2’,3’-dideoxyinosine (ddI) in excellent yield.

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Section: Scheme 1 Regioselective Enzymatic Acylation Ofmentioning

confidence: 99%

Sustainable Protocol for the Synthesis of 2′,3′-Dideoxynucleoside and 2′,3′-Didehydro-2′,3′-dideoxynucleoside Derivatives

Martín-Nieves

Sanghvi²,

Fernández

et al. 2022

Molecules

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PVP−I Catalyzed Oxidation of N‐substituted Benzylamines to Benzamides

Lu,

Yuan,

Wang

et al. 2024

ChemistrySelect

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An oxidative transformation from N‐substituted benzylamine into the corresponding benzamides was developed here using the oxidative system combined from the catalytic amount of PVP−I (polyinyl pyrrolidone) with TBHP. This newly developed method had the advantages of mild reaction conditions and broad substrate scope. The key intermediate of Enzalutamide as androgen receptor inhibitors was prepared using this catalytic condition starting from commercial available 2‐fluoro‐4‐nitrobenzaldehyde with the yield of 78.5 % for three‐step reactions.

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Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I

Wang

Cao

et al. 2021

Tetrahedron

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Catalytic removal of tert-butyldimethylsilyl (TBS) ether by PVP-I

Cited by 4 publications

References 36 publications

Sustainable Protocol for the Synthesis of 2′,3′-Dideoxynucleoside and 2′,3′-Didehydro-2′,3′-dideoxynucleoside Derivatives

Sustainable Protocol for the Synthesis of 2′,3′-Dideoxynucleoside and 2′,3′-Didehydro-2′,3′-dideoxynucleoside Derivatives

PVP−I Catalyzed Oxidation of N‐substituted Benzylamines to Benzamides

Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I

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