TY - JOUR
T1 - Reactions of Nucleophiles with Reactive Intermediates in the 3,4,6-Tri-O-benzyl-D-glucal-TfOH-n-Bu4NI Reaction System
AU - Kelson, Idil Kasuto
AU - Feit, Ben Ami
PY - 2003
Y1 - 2003
N2 - The unique reactive intermediate formed in the 3,4,6-tri-O-benzyl-D-glucal- TfOH (triflic acid)-n-Bu4NI reaction system (in dichloromethane) reacted with nucleophiles in a regio- and stereoselective manner. These selectivities resulted in hitherto unknown compounds, such as benzyl 4,6-di-O-benzyl-2,3-dideoxy-3-iodo-α-glucopyranoside, which was obtained in the presence of an iodide ion as a nucleophile. The corresponding 2-deoxy α-glycosides were obtained exclusively in the corresponding reaction with hydroxylic nucleophiles.
AB - The unique reactive intermediate formed in the 3,4,6-tri-O-benzyl-D-glucal- TfOH (triflic acid)-n-Bu4NI reaction system (in dichloromethane) reacted with nucleophiles in a regio- and stereoselective manner. These selectivities resulted in hitherto unknown compounds, such as benzyl 4,6-di-O-benzyl-2,3-dideoxy-3-iodo-α-glucopyranoside, which was obtained in the presence of an iodide ion as a nucleophile. The corresponding 2-deoxy α-glycosides were obtained exclusively in the corresponding reaction with hydroxylic nucleophiles.
KW - 2-deoxyglycopyranosides
KW - Carbohydrates
KW - Glucal
KW - Iodosugars
KW - Nucleophiles
KW - Reactive intermediates
UR - http://www.scopus.com/inward/record.url?scp=1642555525&partnerID=8YFLogxK
U2 - 10.1081/CAR-120026596
DO - 10.1081/CAR-120026596
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AN - SCOPUS:1642555525
SN - 0732-8303
VL - 22
SP - 827
EP - 841
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 9
ER -