Efficient synthesis of omega-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates.
Lewis acid-promoted reactions of peracetylated sugars (glucose, galactose, maltose, lactose) with omega-bromo-1-alkanols (C(8), C(12)) were investigated. ZnCl(2) was found to promote the 1,2-trans-glycosylation of the alcohols in toluene at about 60 degrees C in a stereocontrolled manner with better yields than commonly employed promoters such as SnCl(4). The omega-bromoalkyl acetylated glycosides were readily converted to omega-mercaptoalkyl glycosides, which are useful for the preparation of glycoclusters.
Murakami
Teiichi
T
Institute for Biological Resources and Functions, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan. t-murakami@aist.go.jp
Hirono
Reiko
R
Sato
Yukari
Y
Furusawa
Kiyotaka
K
D000085:Acetates; D000107:Acetylation; D000438:Alcohols / Q000378:metabolism; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006601:Hexoses / Q000378:metabolism*; D008958:Models, Molecular; D009844:Oligosaccharides / Q000138:chemical synthesis; D011506:Proteins / Q000737:chemistry
D000085:Acetates; D000438:Alcohols; D002241:Carbohydrates; D004187:Disaccharides; D006027:Glycosides; D006601:Hexoses; D009844:Oligosaccharides; D011506:Proteins; D005947:Glucose