An improved synthesis of 5-thio-D-ribose from D-ribono-1,4-lactone.
5-Thio-D-ribopyranose was synthesized from D-ribono-1,4-lactone (1) by two approaches: (i) 5-bromo-5-deoxy-D-ribono-1,4-lactone (2) was successively transformed into 5-bromo-5-deoxy, 5-S-acetyl-5-thio or 5-thiocyanato-D-ribofuranose derivatives; appropriate treatment then lead to 5-thio-D-ribopyranose (7) in 46-48% overall yield and; (ii) 2 was transformed into the 5-S-acetyl-5-thio-D-ribono-1,4-lactone derivative (11). Reduction and deprotection of 11 afforded 5-thio-D-ribopyranose (7) in 57% overall yield.
Lalot
Jérôme
J
Laboratoire des Glucides, Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens, France.
Stasik
Imane
I
Demailly
Gilles
G
Beaupère
Daniel
D
D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D012266:Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
C474980:5-thio-D-ribose; D007783:Lactones; C474981:D-ribono-1,4-lactone; D012266:Ribose