Application of SO3H Silica Gel to Deprotection of Silyl Ethers

Application of SO 3 H Silica Gel to Deprotection of Silyl Ethers. -O-Si bonds in various alkyl and aryl silyl ethers are efficiently cleaved by a new SO3H silica gel on which alkylsulfonic acid group are immobilized. -(FUJII, H.; YAMADA, T.; HAYASHIDA, K.; KUWADA, M.; HAMASAKI, A.; NOBUHARA, K.; OZEKI, S.; NAGASE*, H.; Heterocycles 85 (2012) 11, 2685-2691, http://dx.doi.org/10.3987/com-12-12577 ; Sch. Pharm., Kitasato Univ., Minato, Tokyo 108, Japan; Eng.) -H. Toeppel 11-038

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ChemInform Abstract: Application of SO₃H Silica Gel to Deprotection of Silyl Ethers.

Fujii

Yamada

Hayashida

et al. 2013

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A New Lead Identification Strategy: Screening an sp³‐rich and Lead‐like Compound Library Composed of 7‐Azanorbornane Derivatives

et al. 2019

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Although the advantages of sp3‐rich, sterically complicated molecules in drug development have been pointed out, modern screening libraries are filled with planar, sp2‐rich components. Compounds that are sp3‐rich are difficult to synthesize, and thus we aimed to invent an efficient method to construct sp3‐rich libraries. By modifying sp3‐rich 7‐azanorbornane scaffolds through click chemistry, we efficiently prepared a small set of compounds. These compounds were not only sp3‐rich, but also had sufficient “lead‐like” properties in view of molecular weights and hydrophobicity. Screening assays of this library provided weak κ opioid receptor agonists and growth hormone secretagogue receptor agonists with high hit rates. These results indicate that the 7‐azanorbornane scaffold may be a “privileged structure” for lead identification in drug discovery.

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Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste‐Free Synthesis of Pristane

et al. 2017

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Hydroxy‐substituted sulfonic acid functionalized silica (HO‐SAS) in combination with THF containing a small amount of water as a solvent proved to be a reliable system for the dehydration of allylic alcohols. This process generally caused dehydration within 1 min through a column reactor charged with HO‐SAS. The flow dehydration was sequenced by flow hydrogenation, which resulted in the synthesis of pristane. A scalable flow synthesis of pristane was successfully performed and afforded 10 g of pristane after an operation of 2 h. We also performed dehydration and hydrogenation by using a mixed column of HO‐SAS and 10 % Pd/C.

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Application of SO3H Silica Gel to Deprotection of Silyl Ethers

Cited by 8 publications

References 29 publications

ChemInform Abstract: Application of SO₃H Silica Gel to Deprotection of Silyl Ethers.

ChemInform Abstract: Application of SO₃H Silica Gel to Deprotection of Silyl Ethers.

A New Lead Identification Strategy: Screening an sp³‐rich and Lead‐like Compound Library Composed of 7‐Azanorbornane Derivatives

Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste‐Free Synthesis of Pristane

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Application of SO3H Silica Gel to Deprotection of Silyl Ethers

Cited by 8 publications

References 29 publications

ChemInform Abstract: Application of SO3H Silica Gel to Deprotection of Silyl Ethers.

ChemInform Abstract: Application of SO3H Silica Gel to Deprotection of Silyl Ethers.

A New Lead Identification Strategy: Screening an sp3‐rich and Lead‐like Compound Library Composed of 7‐Azanorbornane Derivatives

Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste‐Free Synthesis of Pristane

Contact Info

Product

Resources

About

ChemInform Abstract: Application of SO₃H Silica Gel to Deprotection of Silyl Ethers.

ChemInform Abstract: Application of SO₃H Silica Gel to Deprotection of Silyl Ethers.

A New Lead Identification Strategy: Screening an sp³‐rich and Lead‐like Compound Library Composed of 7‐Azanorbornane Derivatives