Mechanism of the Hydrogen Chloride/Methanol-Catalyzed Mutarotation Reaction of N-(p-Chlorophenyl)-β-D-glucopyranosylamine

Smiataczowa, Kazimiera; Maj, K.; Skurski, Piotr

doi:10.1002/1099-0690(200111)2001:22<4269::aid-ejoc4269>3.0.co;2-g

Search citation statements

Order By: Relevance

Paper Sections

Select...

Reactions Of Glucosides and Nucleosides1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2004

2018

Publication Types

Select...

Article4

Other1

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 7 publications

(1 citation statement)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…HCl-catalysed mutarotation of N -(p-chlorophenyl)-β-D-glucopyranosylamine (12) in methanol proceeds via a low-energy acyclic immonium ion formed by protonation of the in-ring oxygen atom; activation parameters are reported. 14 Rates and equilibria have been calculated for the mutarotation of glucose. 15 When 2,3 : 4,5-di-O-isopropylidene-D-ribose diethyl dithioacetal [13, R = CH-(SEt) 2 ] is treated under 'standard' hydrolytic deprotection conditions of mercuric (12) ( chloride and oxide in aqueous acetone, a reductive dimeric coupling product is obtained in addition to the expected aldehyde (13, R = CHO).…”

Section: Reactions Of Glucosides and Nucleosidesmentioning

confidence: 99%

Reactions of Aldehydes and Ketones and their Derivatives

Knipe¹

2015

Organic Reaction Mechanisms Series

View full text Add to dashboard Cite

Formation and Reactions of Acetals and Related SpeciesThe α,α -dihaloketone 2,4-dichlorobicyclo[3.2.1]oct-6-en-3-one (1, a mixture of ax-ax, ax-eq, and eq-eq isomers) undergoes a 1,3-transposition in alkoxide-alcohol media to give α-ketoacetals (2, R = CH 3 , CH 2 CF 3 , −CH 2 CH 2 −), all of which are readily hydrolysable to the corresponding α-diones. 1 The acetal is favoured by an O,O-geminal stabilization relative to the α,α -dialkoxy ketone: none of the latter

show abstract

Section: Reactions Of Glucosides and Nucleosidesmentioning

confidence: 99%