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Stereoselective synthesis of D-glycero-D-manno-heptose-1ß,7-bisphosphate (HBP) from D-mannurono-2,6-lactone.
Shinotsuka, Yuta; Nakajima, Riko; Ogawa, Kohei; Takise, Kaede; Takeuchi, Yutaka; Tanaka, Hiroshi; Sasaki, Kaname.
Afiliação
  • Shinotsuka Y; Department of Chemistry, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan. Kaname.sasaki@sci.toho-u.ac.jp.
  • Nakajima R; Department of Chemistry, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan. Kaname.sasaki@sci.toho-u.ac.jp.
  • Ogawa K; Department of Chemistry, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan. Kaname.sasaki@sci.toho-u.ac.jp.
  • Takise K; Department of Chemistry, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan. Kaname.sasaki@sci.toho-u.ac.jp.
  • Takeuchi Y; Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1-H101, Ookayama, Muguro-ku, Tokyo 152-8552, Japan.
  • Tanaka H; Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1-H101, Ookayama, Muguro-ku, Tokyo 152-8552, Japan.
  • Sasaki K; Department of Chemistry, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan. Kaname.sasaki@sci.toho-u.ac.jp.
Org Biomol Chem ; 22(13): 2544-2548, 2024 Mar 27.
Article em En | MEDLINE | ID: mdl-38414338
ABSTRACT
The synthesis of D-glycero-D-manno-heptose-1ß,7-bisphosphate (HBP) from D-mannose is described. This synthetic approach is notable for the elongation of the seventh carbon, employing mannurono-2,6-lactone, the substrate-controlled establishment of the C-6 configuration, and the nucleophilic introduction of phosphate at the C-1 position through the utilization of 4,6-O-benzylidene-α-triflate.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Biomol Chem Ano de publicação: 2024 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Biomol Chem Ano de publicação: 2024 Tipo de documento: Article