Transetherification on Polyols by Intra- and Intermolecular Nucleophilic Substitutions
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{"title"=>"Transetherification on polyols by intra- And intermolecular nucleophilic substitutions", "type"=>"journal", "authors"=>[{"first_name"=>"Takahiro", "last_name"=>"Muraoka", "scopus_author_id"=>"7007042797"}, {"first_name"=>"Kota", "last_name"=>"Adachi", "scopus_author_id"=>"55605207800"}, {"first_name"=>"Rainy", "last_name"=>"Chowdhury", "scopus_author_id"=>"57198218339"}, {"first_name"=>"Kazushi", "last_name"=>"Kinbara", "scopus_author_id"=>"7004022332"}], "year"=>2014, "source"=>"PLoS ONE", "identifiers"=>{"doi"=>"10.1371/journal.pone.0091912", "issn"=>"19326203", "sgr"=>"84899723954", "scopus"=>"2-s2.0-84899723954", "pui"=>"373006654", "pmid"=>"24663293"}, "id"=>"7849c6d1-97db-3cdd-9ace-ac7facddfedb", "abstract"=>"Transetherification on polyols involving intra- and intermolecular nucleophilic substitutions is reported. Di- or trialkoxide formation of propane-1,3-diol or 2-(hydroxymethyl)propane-1,3-diol derivatives by NaH triggers the reaction via oxetanes formation, where the order to add NaH and a polyol significantly influences the yields of products. It was demonstrated that the protective group on the pentaerythritol skeleton is apparently transferred to the hydrophilic and hydrophobic chain molecules bearing a leaving group in one-step, and a protective group conversion from tosyl to benzyl was successful using a benzyl-appending triol to afford a desired product in 67% yield.", "link"=>"http://www.mendeley.com/research/transetherification-polyols-intra-intermolecular-nucleophilic-substitutions", "reader_count"=>5, "reader_count_by_academic_status"=>{"Student > Ph. D. Student"=>2, "Student > Master"=>1, "Student > Bachelor"=>2}, "reader_count_by_user_role"=>{"Student > Ph. D. Student"=>2, "Student > Master"=>1, "Student > Bachelor"=>2}, "reader_count_by_subject_area"=>{"Chemistry"=>5}, "reader_count_by_subdiscipline"=>{"Chemistry"=>{"Chemistry"=>5}}, "group_count"=>0}

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Figshare

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  • {"files"=>["https://ndownloader.figshare.com/files/1433227"], "description"=>"<p>Structures of 6 and 7 are shown in <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0091912#pone-0091912-g003\" target=\"_blank\">Figure 3</a>. Matrix: α-cyano-4-hydroxycinnamic acid.</p>", "links"=>[], "tags"=>["biotechnology", "biomaterials", "Small molecules", "chemistry", "Chemical compounds", "Organic compounds", "ethers", "Functional groups", "Chemical reactions", "Organic reactions", "organic chemistry", "Organic synthesis", "Materials Science", "Materials chemistry", "Chemical synthesis", "crude", "extracted"], "article_id"=>972668, "categories"=>["Biological Sciences"], "users"=>["Takahiro Muraoka", "Kota Adachi", "Rainy Chowdhury", "Kazushi Kinbara"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091912.g002", "stats"=>{"downloads"=>1, "page_views"=>29, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_MALDI_TOF_MS_spectrum_of_the_crude_product_extracted_by_CHCl_3_for_the_reaction_in_Table_1_Entry_1_/972668", "title"=>"MALDI-TOF-MS spectrum of the crude product extracted by CHCl<sub>3</sub> for the reaction in Table 1, Entry 1.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-24 03:49:41"}
  • {"files"=>["https://ndownloader.figshare.com/files/1433228"], "description"=>"<p>A plausible reaction mechanism of the intra- and intermolecular nucleophilic substitutions to prompt transetherification.</p>", "links"=>[], "tags"=>["biotechnology", "biomaterials", "Small molecules", "chemistry", "Chemical compounds", "Organic compounds", "ethers", "Functional groups", "Chemical reactions", "Organic reactions", "organic chemistry", "Organic synthesis", "Materials Science", "Materials chemistry", "Chemical synthesis", "plausible", "intra-", "intermolecular", "nucleophilic", "substitutions"], "article_id"=>972669, "categories"=>["Biological Sciences"], "users"=>["Takahiro Muraoka", "Kota Adachi", "Rainy Chowdhury", "Kazushi Kinbara"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091912.g003", "stats"=>{"downloads"=>4, "page_views"=>200, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_A_plausible_reaction_mechanism_of_the_intra_and_intermolecular_nucleophilic_substitutions_to_prompt_transetherification_/972669", "title"=>"A plausible reaction mechanism of the intra- and intermolecular nucleophilic substitutions to prompt transetherification.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-24 03:49:41"}
  • {"files"=>["https://ndownloader.figshare.com/files/1433229"], "description"=>"<p>Reaction time was 12 h. Yields were calculated based on the isolated amounts. ND: not detected.</p>", "links"=>[], "tags"=>["biotechnology", "biomaterials", "Small molecules", "chemistry", "Chemical compounds", "Organic compounds", "ethers", "Functional groups", "Chemical reactions", "Organic reactions", "organic chemistry", "Organic synthesis", "Materials Science", "Materials chemistry", "Chemical synthesis", "tetraethylene", "glycol", "tosylate", "2a", "monoalcohol", "11"], "article_id"=>972670, "categories"=>["Biological Sciences"], "users"=>["Takahiro Muraoka", "Kota Adachi", "Rainy Chowdhury", "Kazushi Kinbara"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091912.g004", "stats"=>{"downloads"=>5, "page_views"=>158, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Ether_formation_between_tetraethylene_glycol_tosylate_2a_and_a_monoalcohol_8_b_propane_1_3_diol_11_and_c_2_hydroxymethyl_propane_1_3_diol_13_/972670", "title"=>"Ether formation between tetraethylene glycol tosylate 2a and a) monoalcohol 8, b) propane-1,3-diol 11 and c) 2-(hydroxymethyl)propane-1,3-diol 13.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-24 03:49:41"}
  • {"files"=>["https://ndownloader.figshare.com/files/1433230"], "description"=>"a)<p>Reaction conditions: 30 mL THF, 0.972 mmol <b>1</b>, 1.94 mmol <b>2</b>, 9.72 mmol NaH; reflux (ca. 339 K); reaction time: 12 h. <sup>b)</sup> Reaction conditions: 30 mL THF, 0.486 mmol <b>1</b>, 0.972 mmol <b>2</b>, 4.86 mmol NaH; reflux (ca. 339 K); reaction time: 12 h. <sup>c)</sup> Isolated yields.</p>", "links"=>[], "tags"=>["biotechnology", "biomaterials", "Small molecules", "chemistry", "Chemical compounds", "Organic compounds", "ethers", "Functional groups", "Chemical reactions", "Organic reactions", "organic chemistry", "Organic synthesis", "Materials Science", "Materials chemistry", "Chemical synthesis"], "article_id"=>972671, "categories"=>["Biological Sciences"], "users"=>["Takahiro Muraoka", "Kota Adachi", "Rainy Chowdhury", "Kazushi Kinbara"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0091912.t001", "stats"=>{"downloads"=>7, "page_views"=>16, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Ether_formation_between_1_and_2_/972671", "title"=>"Ether formation between 1 and 2.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2014-03-24 03:49:41"}

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Relative Metric

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