Literature DB >> 22994426

A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure.

Kohei Yamada1, Hikaru Fujita, Munetaka Kunishima.   

Abstract

Formal trimerization of the smallest unit of benzyl imidate leads to 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT), which can be used as an acid-catalyzed O-benzylating reagent. The reaction of various functionalized alcohols with 0.4 equiv of TriBOT in the presence of trifluoromethanesulfonic acid afforded the benzyl ethers in good yields. TriBOT is an inexpensive stable crystalline solid with high atom economy.

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Year:  2012        PMID： 22994426     DOI： 10.1021/ol302222p

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

1.  Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions.

Authors:  Kyle T Howard; Brian C Duffy; Matthew R Linaburg; John D Chisholm
Journal:  Org Biomol Chem       Date:  2016-02-07       Impact factor: 3.876

2.  Regioselective Benzylation of 2-Deoxy-2-Aminosugars Using Crown Ethers: Application to a Shortened Synthesis of Hyaluronic Acid Oligomers.

Authors:  Chinmoy Mukherjee; Lin Liu; Nicola L B Pohl
Journal:  Adv Synth Catal       Date:  2014-07-07       Impact factor: 5.837

3.  Pennelliiside D, a New Acyl Glucose from Solanum pennellii and Chemical Synthesis of Pennelliisides.

Authors:  Rishni Masimbula; Hiroto Kobayashi; Tenki Nakashima; Yurika Nambu; Naoki Kitaoka; Hideyuki Matsuura
Journal:  Molecules       Date:  2022-06-09       Impact factor: 4.927

4.  Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition.

Authors:  Shuichi Hagihara; Kengo Hanaya; Takeshi Sugai; Mitsuru Shoji
Journal:  J Antibiot (Tokyo)       Date:  2017-08-02       Impact factor: 2.649

5.  Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy.

Authors:  Pei Cao; Zhen-Jie Li; Wen-Wu Sun; Shashwat Malhotra; Yuan-Liang Ma; Bin Wu; Virinder S Parmar
Journal:  Nat Prod Bioprospect       Date:  2014-12-16

6.  Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid.

Authors:  Kohei Yamada; Naoto Kamimura; Munetaka Kunishima
Journal:  Beilstein J Org Chem       Date:  2017-07-27       Impact factor: 2.883

7.  Synthesis of α-D-GalpN3-(1-3)-D-GalpN3: α- and 3-O-selectivity using 3,4-diol acceptors.

Authors:  Emil Glibstrup; Christian Marcus Pedersen
Journal:  Beilstein J Org Chem       Date:  2018-11-08       Impact factor: 2.883

8.  Design and 22-step synthesis of highly potent D-ring modified and linker-equipped analogs of spongistatin 1.

Authors:  Linda M Suen; Makeda A Tekle-Smith; Kevin S Williamson; Joshua R Infantine; Samuel K Reznik; Paul S Tanis; Tyler D Casselman; Dan L Sackett; James L Leighton
Journal:  Nat Commun       Date:  2018-11-09       Impact factor: 14.919

9.  A Direct Method for β-Selective Glycosylation with an N-Acetylglucosamine Donor Armed by a 4-O-TBDMS Protecting Group.

Authors:  Hidenori Tanaka; Yu Hamaya; Hiyoshizo Kotsuki
Journal:  Molecules       Date:  2017-03-08       Impact factor: 4.411

10.  Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition.

Authors:  Martin Riemer; Veselina V Uzunova; Nastja Riemer; Guy J Clarkson; Nicole Pereira; Richard Napier; Michael Shipman
Journal:  Chem Commun (Camb)       Date:  2018-06-26       Impact factor: 6.222
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