Relevance of the glycosyl donor to the regioselectivity of glycosidation of primary-secondary diol acceptors and application of these ideas to in situ three-component double differential glycosidation.
[reaction: see text] Three pairs of primary-secondary diol acceptors have been exposed to armed, disarmed, and n-pentenyl ortho ester glycosyl donors in glycosidation reactions. It is shown that the regioselectivity of those glycosylations is greatly influenced by the armed, disarmed, or ortho ester nature of the glycosyl donors. The selectivities observed have been used to devise efficient in situ three-component glycosylations involving two donors and one acceptor.
Uriel
Clara
C
Instituto de Química Orgánica General (CSIC), Madrid, Spain.
Agocs
Attila
A
Gómez
Ana M
AM
López
J Cristóbal
JC
Fraser-Reid
Bert
B
D000438:Alcohols / Q000737:chemistry*; D002240:Carbohydrate Sequence; D005947:Glucose / Q000737:chemistry; D006026:Glycoside Hydrolases; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D008358:Mannose / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D006027:Glycosides; D006026:Glycoside Hydrolases; D005947:Glucose; D008358:Mannose