MIPs logo MIPdatabase      Use this space
Custom Search
Reference type: Journal
Authors: Nakashima K, Shinkai S, Ikeda A
Article Title: Saccharide libraries as potential templates for regio- and chiroselective introduction of two functional groups into [60]fullerene.
Publication date: 1999
Journal: Journal of Organic Chemistry
Volume: 64
Issue: (3)
Page numbers: 984-990.
DOI: 10.1021/jo9822277

Abstract: This paper reports regio- and chiroselective introduction of two boronic acid groups into [60]fullerene controlled by a saccharide used as a template molecule. The double [4+2] cycloadditions between [60]fullerene and 1:2 saccharide-boronic acid complexes 6-9 afforded [60]fullerene-bisadducts 12. Their structures were identified on the basis of H-1 and C-13 NMR, UV-vis, and CD spectroscopy, mass spectrometry, and chiral HPLC analysis. When 3-O-methyl-D-glucose (4) was used as the template molecule, high regioselectivity was achieved which gave trans-4 isomer 12a as a main isomer in 72.5% yield. The chiro- as well as regioselective preparation of e isomer 12c was attained in 81.4% ee from the 55.7% yield racemic mixture by the reaction using the D-mannitol-3,4-carbonate template (3). When the enantiomers, D-threitol(D-2) and L-threitol(L-2) were used as the templates, cis-3 isomers 12b and ent-12b with opposite chirality were yielded in 44.2 and 45.2% ee, respectively. On the other hand, 1-O- methyl-alpha-D-mannopyranoside template (5) featured nonselective cycloaddition


  Silicon periodic table shirt  Scientist peptide mug  I shop perodically customisable tote bag

Molecules Special Issue call      Appeal for information






Join the Society for Molecular Imprinting
Logo of the Society for Molecular Imprinting

New items RSS feed
new items RSS feed  View latest updates

Sign-up for e-mail updates:
Choose between receiving an occasional newsletter or more frequent e-mail alerts.
Click here to go to the sign-up page.


Is your name elemental or peptidic? Enter your name and find out by clicking either of the buttons below!
Other products you may like:
view listings for MIP books on eBay:
US listings   UK listings

Searching for Molecular Imprinting books on Amazon.com:
Molecular Imprinting
Imprinted Polymers
Polymer Chemistry
Organic Chemistry
Biosensors

Find what you need at Amazon.com

Lab supplies from Amazon