Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

• Shahien Shahsavari,
• Dhananjani N. A. M. Eriyagama,
• Bhaskar Halami,
• Vagarshak Begoyan,
• Marina Tanasova,
• Jinsen Chen and
• Shiyue Fang

Beilstein J. Org. Chem. 2019, 15, 1116–1128, doi:10.3762/bjoc.15.108

• electrophilic oligodeoxynucleotides (ODNs) was achieved using dimethyl-Dmoc (dM-Dmoc) as amino protecting group. Due to the high steric hindrance of the 2-(propan-2-ylidene)-1,3-dithiane side product from deprotection, the use of excess nucleophilic scavengers such as aniline to prevent Michael addition of the

• thioester. Using the technology, the sensitive groups can be installed at any location within the ODN sequences without using any sequence- or functionality-specific conditions and procedures. Keywords: Dmoc; electrophilic; oligonucleotides; protecting group; solid-phase synthesis; Introduction After over

• especially for the synthesis of ODNs approaching 20-mer or longer, may not be easy to achieve. To develop a universal technology for the synthesis of ODNs that contain a wide variety of sensitive functionalities, we recently reported the use of 1,3-dithian-2-ylmethoxycabonyl (Dmoc) as protecting groups and

An amine protecting group deprotectable under nearly neutral oxidative conditions

• Shahien Shahsavari,
• Chase McNamara,
• Mark Sylvester,
• Emily Bromley,
• Savannah Joslin,
• Bao-Yuan Lu and
• Shiyue Fang

Beilstein J. Org. Chem. 2018, 14, 1750–1757, doi:10.3762/bjoc.14.149

• 10.3762/bjoc.14.149 Abstract The 1,3-dithiane-based dM-Dmoc group was studied for the protection of amino groups. Protection was achieved under mild conditions for aliphatic amines, and under highly reactive conditions for the less reactive arylamines. Moderate to excellent yields were obtained

• collection of transformations to be carried out on the protected substrates that are unattainable using any known protecting groups. Keywords: amine; carbamate; dM-Dmoc; oxidation; protecting group; Introduction In multistep organic synthesis, amino groups usually have to be protected [1]. Protecting

• carbamate and 6-nitroveratryl carbamate) [9][10] and fluoride (e.g., trimethylsilylethyloxycarbonyl (Teoc) group) [11][12]. The 1,3-dithian-2-ylmethoxycarbonyl (Dmoc) group first reported by Kunz and co-workers provides a different dimension of orthogonality of amine protection in terms of deprotection