Synthesis of heparin oligosaccharides.
An efficient preparation of rare 2-O-benzoyl-3-O-benzyl-1,6-anhydro-beta-l-idopyranose from commercially available diacetone alpha-d-glucose in five straightforward steps is described here. With this key building block in hand, the total syntheses of heparin oligosaccharides with three, five, seven, and nine sugar units are successfully carried out.
Lee
Jinq-Chyi
JC
Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan.
Lu
Xin-An
XA
Kulkarni
Suvarn S
SS
Wen
Yuh-Sheng
YS
Hung
Shang-Cheng
SC
D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D006493:Heparin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009844:Oligosaccharides / Q000138:chemical synthesis*
D006027:Glycosides; D009844:Oligosaccharides; D006493:Heparin