An efficient method for the selective synthesis of 2-deoxy-2-iodo-glycosides by O-glycosidation of D-glucal using I₂-Cu(OAc)₂.
An efficient and convenient method for the synthesis of 2-deoxy-2-iodo-O-glycosides from tri-O-acetyl-D-glucal with various alcohols by using I₂-Cu(OAc)₂ is described. The 21 examples of corresponding glycosides were obtained in high yields, with good anomeric selectivity.
Sirion
Uthaiwan
U
Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Sangsook, Chonburi 20131, Thailand.
Purintawarrakun
Sittidate
S
Sahakitpichan
Poolsak
P
Saeeng
Rungnapha
R
D000438:Alcohols / Q000737:chemistry; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D003837:Deoxy Sugars; D009942:Organometallic Compounds; C001289:d-glucal; C015092:cupric acetate; D007455:Iodine; D003847:Deoxyglucose