Synthesis of homogalacturonan fragments

Article abstract of DOI:10.1080/07328300008544125

Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides α(1→4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the a(1''→4')-linked trimer 39 (48%). Approximately 8% of the β(1''→4')-coupled isomer was observed in the ¹³C NMR spectrum of the reaction mixture.

Full text of DOI:10.1080/07328300008544125

This article was downloaded by: [Queensland University of Technology]
On: 19 October 2014, At: 16:19
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Journal of Carbohydrate Chemistry
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lcar20
Synthesis of Homogalacturonan
Fragments
Sven Kramer , Birte Nolting , Andrej-Jakob Ott & Christian
Vogel
a Department of Chemistry, Division of Organic Chemistry ,
University of Rostock , Buchbinderstraße 9, 18051 Rostock,
Germany E-mail:
b Department of Chemistry, Division of Organic Chemistry ,
University of Rostock , Buchbinderstraße 9, 18051 Rostock,
Germany E-mail:
c Department of Chemistry, Division of Organic Chemistry ,
University of Rostock , Buchbinderstraße 9, 18051 Rostock,
Germany E-mail:
d Department of Chemistry, Division of Organic Chemistry ,
University of Rostock , Buchbinderstraße 9, 18051 Rostock,
Germany E-mail:
Published online: 27 Feb 2008.
To cite this article: Sven Kramer , Birte Nolting , Andrej-Jakob Ott & Christian Vogel (2000)
Synthesis of Homogalacturonan Fragments, Journal of Carbohydrate Chemistry, 19:7, 891-921,
DOI: 10.1080/07328300008544125
To link to this article: http://dx.doi.org/10.1080/07328300008544125
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information
(the “Content”) contained in the publications on our platform. However, Taylor
& Francis, our agents, and our licensors make no representations or warranties
whatsoever as to the accuracy, completeness, or suitability for any purpose of the
Content. Any opinions and views expressed in this publication are the opinions and
views of the authors, and are not the views of or endorsed by Taylor & Francis. The
accuracy of the Content should not be relied upon and should be independently
verified with primary sources of information. Taylor and Francis shall not be liable
for any losses, actions, claims, proceedings, demands, costs, expenses, damages,

and other liabilities whatsoever or howsoever caused arising directly or indirectly in
connection with, in relation to or arising out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden.
Terms & Conditions of access and use can be found at http://www.tandfonline.com/
page/terms-and-conditions