Details

Autor(en) / Beteiligte

• Mikata, Yuji
• Shinohara, Yoshie
• Yoneda, Kazumi
• Nakamura, Yuka
• Esaki, Kimiko
• Tanahashi, Maki
• Brudziñska, Izabela
• Hirohara, Shiho
• Yokoyama, Mika
• Mogami, Kaoru
• Tanase, Tomoaki
• Kitayama, Takashi
• Takashiba, Katsuki
• Nabeshima, Kenji
• Takagi, Rie
• Takatani, Masahiko
• Okamoto, Tadashi
• Kinoshita, Isamu
• Doe, Matsumi
• Hamazawa, Akihisa
• Morita, Masanori
• Nishida, Fumiko
• Sakakibara, Toru
• Orvig, Chris
• Yano, Shigenobu

Titel

Sugar-Pendant Diamines

Ist Teil von

• Journal of organic chemistry, 2001-06, Vol.66 (11), p.3783-3789

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2001

Quelle

MEDLINE

Beschreibungen/Notizen

• A set of 1,3-propanediamine derivatives connected to carbohydrates (5) has been prepared in four steps from peracetylated sugar and 1,3-dibromo-2-propanol in 60−73% yields. d-Glucose, d-mannose, d-galactose, d-xylose, d-ribose, and maltose are utilized as sugar molecules in this work. The diamine moiety was connected to the C1 carbon of the glycopyranose ring via an O-glycoside bond. All of the anomeric configurations and sugar puckering conformations, except in the d-maltose derivative, were determined by X-ray crystallography of the diazido or dibromo precursors. While glycosidation of peracetylated galactopyranose with 1,3-dibromo-2-propanol in the presence of boron trifluoride afforded both anomers, the neighboring group participation of the 2-acetoxy group yielded a single anomer for the other substrates. This method has been used to synthesize a library of sugar-pendant diamines including an OH-protected derivative (6), and an N,N‘-diisopropyl-substituted derivative (7). A similar series of reactions using 2,3-dibromo-1-propanol gave ethylenediamine-type derivatives (11), and bis(bromomethyl)bis(hydroxymethyl)methane (12) gave bisglucose-pendant derivatives (16).