Novel synthesis of L-ribose from D-mannono-1,4-lactone.
[reaction: see text] D-Mannono-1,4-lactone was efficiently converted into L-ribose in eight steps. A key step of this synthesis is the cyclization of a gamma-hydroxyalkoxamate under Mitsunobu conditions. It is noteworthy that the O-alkylation product was obtained in 94% yield and that none of the N-alkylation product was detected in this cyclization.
Takahashi
Hideyo
H
Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-0195, Japan.
Iwai
Yoshinori
Y
Hitomi
Yuko
Y
Ikegami
Shiro
S
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry*; D000478:Alkylation; D003500:Cyclization; D007202:Indicators and Reagents; D012266:Ribose / Q000138:chemical synthesis*
D007202:Indicators and Reagents; C091284:mannono-1,4-lactone; D012266:Ribose; D015107:4-Butyrolactone