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Literature DB >> 20414457

An Alkoxide Anion Triggered tert-Butyloxycarbonyl Group Migration. Mechanism and Application.

Abstract

We report a fast N→O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.

Entities: Chemical Disease Gene

Year: 2010 PMID： 20414457 PMCID： PMC2856655 DOI： 10.1016/j.tetlet.2010.03.009

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

6 in total

1. Analogues of 2-aminopyridine-based selective inhibitors of neuronal nitric oxide synthase with increased bioavailability.

Authors: Graham R Lawton; Hantamalala Ralay Ranaivo; Laura K Chico; Haitao Ji; Fengtian Xue; Pavel Martásek; Linda J Roman; D Martin Watterson; Richard B Silverman
Journal: Bioorg Med Chem Date: 2009-02-14 Impact factor: 3.641

2. Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol.

Authors: L Bunch; P O Norrby; K Frydenvang; P Krogsgaard-Larsen; U Madsen
Journal: Org Lett Date: 2001-02-08 Impact factor: 6.005

3. Potent and selective neuronal nitric oxide synthase inhibitors with improved cellular permeability.

Authors: Fengtian Xue; Jianguo Fang; William W Lewis; Pavel Martásek; Linda J Roman; Richard B Silverman
Journal: Bioorg Med Chem Lett Date: 2009-11-22 Impact factor: 2.823

4. Rearrangement of N,N-di-tert-butoxycarbonylpyridin-4-amines and formation of polyfunctional pyridines.

Authors: Yahua Liu; Qiang Ding; Xu Wu
Journal: J Org Chem Date: 2008-07-09 Impact factor: 4.354

5. 1-Ethoxyethylidene, a new group for the stepwise SPPS of aminooxyacetic acid containing peptides.

Authors: Stéphanie Foillard; Martin Ohsten Rasmussen; Jesus Razkin; Didier Boturyn; Pascal Dumy
Journal: J Org Chem Date: 2008-01-04 Impact factor: 4.354

Review 6. Design of selective neuronal nitric oxide synthase inhibitors for the prevention and treatment of neurodegenerative diseases.

Authors: Richard B Silverman
Journal: Acc Chem Res Date: 2009-03-17 Impact factor: 22.384

6 in total

4 in total

An Alkoxide Anion Triggered tert-Butyloxycarbonyl Group Migration. Mechanism and Application.

1. Analogues of 2-aminopyridine-based selective inhibitors of neuronal nitric oxide synthase with increased bioavailability.

2. Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol.

3. Potent and selective neuronal nitric oxide synthase inhibitors with improved cellular permeability.

4. Rearrangement of N,N-di-tert-butoxycarbonylpyridin-4-amines and formation of polyfunctional pyridines.

5. 1-Ethoxyethylidene, a new group for the stepwise SPPS of aminooxyacetic acid containing peptides.

Review 6. Design of selective neuronal nitric oxide synthase inhibitors for the prevention and treatment of neurodegenerative diseases.

1. Improved synthesis of chiral pyrrolidine inhibitors and their binding properties to neuronal nitric oxide synthase.

2. Acid-Facilitated Debenzylation of N-Boc, N-Benzyl Double Protected 2-Aminopyridinomethylpyrrolidine Derivatives.

3. High yielding allylation of a chiral secondary alcohol containing base sensitive functional groups.

4. Synthesis of the spiroiminal moiety and approaches to the synthesis of marineosins A and B.